Synthesis of 3-chlorobenzyl bromide

Preparation of 3-chlorobenzyl bromide

Preparation of 3-chlorobenzyl bromide

Preparation of 3-chlorobenzyl bromide

0.2 mole of 3-chlorotoluene (m-chlorotoluene) 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 after the addition of a spatulatip of sodium bicarbonate is distilled in vacuo (b.p. 109°C/10mm) yielding 60% of 3-chlorobenzyl bromide (m.p. 17.5°C; 109-110 °C/12 mm; n20/D 1.588).

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)-3-chlorobenzene

InChI

InChI=1S/C7H6BrCl/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

InChI Key

LZIYAIRGDHSVED-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)Cl)CBr

Depositor-Supplied Synonyms

3-Chlorobenzyl bromide, 1-(Bromomethyl)-3-chlorobenzene, 766-80-3, alpha-Bromo-3-chlorotoluene, 3-chlorobenzylbromide, m-Chlorobenzyl bromide, alpha-Bromo-m-chlorotoluene, .alpha.-Bromo-m-chlorotoluene, LZIYAIRGDHSVED-UHFFFAOYSA-N, 1-(bromomethyl)-3-chloro-benzene, Benzene, 1-(bromomethyl)-3-chloro-, ST51039964, NSC60110, 3-chloro-benzylbromide, a-bromo-m-chlorotoluene, PubChem10765, 3-chloro-benzyl bromide, ACMC-1BHYA, AC1L2CS2, AC1Q27OM, AC1Q3I3D, AC1Q3K4L, SCHEMBL2436, KSC377C2L, 1-bromomethyl-3-chlorobenzene, .alpha.-Bromo-3-chlorotoluene, EMOLECULES 481126, 1-bromomethyl-3-chloro-benzene, 1-chloro-3-bromomethyl benzene, 136727_ALDRICH, 3-(bromomethyl)-1-chlorobenzene, CTK2H7125, LZIYAIRGDHSVED-UHFFFAOYSA-, MolPort-000-160-221, 1-(bromo-methyl)-3-chlorobenzene, Toluene, .alpha.-bromo-m-chloro-, ZINC1690005, EINECS 212-171-0, 766-80-3 3-Chlorobenzyl bromide, ANW-36862, AR-1F2693, MFCD00000597, NSC-60110, WT1826, ZINC01690005, AKOS000447218, AS00001, CS22235, MCULE-2987345686, RP26189, RTR-032853, TRA0027091, VZ26697, AJ-30019, AK-77068, AN-47505, BC003560, CJ-06442, CJ-28057, KB-31236, L519, OR004326, OR142441, SC-22381, AB0014749, DB-031897, ST2408600, TL8005254, TR-032853, A9717, AM20041138, FT-0615475, M-6922, 49852-EP2308844A2, 49852-EP2308845A2, 49852-EP2308846A2, 49852-EP2308851A1, 49852-EP2311825A1, I01-0255, W-104349, 3B3-009854, InChI=1/C7H6BrCl/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

Removed Synonyms

CID69838, c1105, 80858-90-8

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