Synthesis of 4-nitrobenzyl bromide

Preparation of 4-nitrobenzyl bromide

Preparation of 4-nitrobenzyl bromide

Preparation of 4-nitrobenzyl bromide

0.2 mole of 4-nitrotoluene is dissolved in a five-fold amount of dry carbon tetrachloride and is charged into a two-necked flask with a reflux condenser and a well-clamped dropping funnel. The dropping funnel should dip into the liquid in order to limit losses of bromine. The flask is heated to the boil and for each atom of hydrogen to be replaced there is added dropwise 0.205 mole of elemental bromine (bromine should be dried by shaking with concentrated sulfuric acid). During the bromination reaction, the mixture is irradiated with a 500-watt photolamp. The rate of addition of the bromine must be adjusted in such a way that the carbon tetrachloride dripping from the reflux condenser always remains practically colourless. The monobromination reaction takes about 30 min to 2 hours.  The hydrogen bromide evolved is led through the reflux condenser, which carries a pierced stopper with a glass tube and PVC tubing, into an Erlenmeyer flask half-filled with water. The inlet tube should not dip into this but end about 1 cm over the surface of the water. At the end of the reaction, the irradiation is stopped. The cooled solution is rapidly washed with ice-water, then with ice-cold aqueous sodium bicarbonate solution, and again with ice-water, and is dried with magnesium sulfate, and the carbon tetrachloride is evaporated off in vacuo. The residue is purified by crystallization from ethanol yielding 80% of 4-nitrobenzyl bromide (m.p. 96-99°C).

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 172-174, (1973)

IUPAC Name

1-(bromomethyl)-4-nitrobenzene

InChI

InChI=1S/C7H6BrNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2

InChI Key

VOLRSQPSJGXRNJ-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1CBr)[N+](=O)[O-]

MeSH Synonyms

4-nitrobenzyl bromide, p-nitrobenzyl bromide

Depositor-Supplied Synonyms

4-Nitrobenzyl bromide, 100-11-8, 1-(Bromomethyl)-4-nitrobenzene, p-Nitrobenzyl bromide, alpha-Bromo-4-nitrotoluene, Benzene, 1-(bromomethyl)-4-nitro-, p-(Bromomethyl)nitrobenzene, 4-(Bromomethyl)nitrobenzene, alpha-Bromo-p-nitrotoluene, alpha-Bromoparanitrotoluene, 4-Nitrobenzylbromide, 1-Bromomethyl-4-nitro-benzene, Toluene, .alpha.-bromo-p-nitro-, NSC 4609, 4NBB, .alpha.-Bromoparanitrotoluene, .alpha.-Bromo-p-nitrotoluene, PARA-NITROBENZYLBROMIDE, .alpha.-Bromo-4-nitrotoluene, A-BROMO-P-NITROTOLUENE, Toluene, alpha-bromo-p-nitro-, CCRIS 7961, Toluene, alpha-bromo-4-nitro-, CHEBI:62822, VOLRSQPSJGXRNJ-UHFFFAOYSA-N, Toluene, .alpha.-bromo-4-nitro-, EINECS 202-820-6, AI3-08875, AP-065/41884110, 4-(bromomethyl)-1-nitrobenzene, p-nitrobenzylbromide, nitro benzyl bromide, 4-nitrobenzylbrornide, p-nitrobenzyl-bromide, 4-nitro benzylbromide, PubChem7473, 4-nitro benzyl bromide, 4-nitro-benzyl bromide, p-bromomethylnitrobenzene, para-Nitrobenzyl bromide, 4-nitro-benzyl bromide;, ACMC-1BSA2, SCHEMBL439, 4-nitrophenylmethyl bromide, 1-bromomethyl4-nitrobenzene, AC1Q1XN9, DSSTox_CID_29351, DSSTox_RID_83467, DSSTox_GSID_49392, 1-bromomethyl-4-nitrobenzene, N13054_ALDRICH, NITROBENZYL-4 BROMIDE, KSC491E9J, A-BROMO-4-NITROTOLUENE, AC1L24F8, AMBZ0160, CHEMBL174047, Jsp000060, SCHEMBL13981949, CTK3J1294, TIMTEC-BB SBB041005, 1-(bromomethyl)-4-nitro-benzene, NSC4609, MolPort-000-872-153, ZINC164454, 1-(Bromomethyl)-4-nitrobenzene #, ACT00372, EBD11151, NSC-4609, STR01237, AKOS BBS-00004545, Tox21_202713, ANW-14163, CX1172, LABOTEST-BB LT02647720, LABOTEST-BB LT03333690, MFCD00007373, SBB041005, STK397280, ZINC00164454, AKOS000269732, AS00716, MCULE-5318696734, RP17515, RTR-000041, TRA0041654, NCGC00260261-01, AC-10995, AJ-16163, AK-96419, BC003251, BC228029, CAS-100-11-8, CJ-02138, KB-59770, OR011571, OR112864, OR192158, SC-00007, ZB008150, AB1002796, DB-016183, LS-154026, ST2408603, TR-000041, AM20020060, FT-0619217, FT-0619218, N0181, ST50214654, A19507, L-1229, 100471-EP2270008A1, 100471-EP2272817A1, 100471-EP2284157A1, 100471-EP2292617A1, 100471-EP2301939A1, 3B4-1152, I01-0777, T5260536, W-108975, InChI=1/C7H6BrNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H

Removed Synonyms

Nitrobenzyl bromide, C7H6BrNO2, |A-Bromo-4-nitrotoluene, CID66011, C027563, 19689-86-2

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