Synthesis of tert-Butyl bromide

Preparation of tert-Butyl bromide (2-bromo-2-methylpropane)

With cooling, 1 mole of the tert-butyl alcohol is treated with 1.25 mole of hydrogen bromide (in the form of the 48%, constant-boiling, acid), and the obtained mixture is boiled and volatile tert-butyl bromide is distilled out from the reaction mixture directly (20-cm Vigreux column, vertical condenser, rate of distillation 2 to 3 drops per second). The obtained crude tert-butyl bromide is twice shaken carefully with about one-fifth of its volume of cold concentrated sulfuric acid or the same volume of concentrated hydrochloric acid in the separating funnel to dissolve the ether produced as a by-product. Then crude tert-butyl bromide is washed with water then it is freed from acid with sodium bicarbonate solution, washed again with water, dried over calcium chloride, and distilled through a 20-cm Vigreux column. The yield of isobutyl bromide is 60%, n20/D 1.4279; mp.p −20 °C; b.p. 71-73 °C; 1.22 g/mL at 20 °C. tert-Butyl bromide should contain 0.5% potassium carbonate as stabilizer.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 195-196, (1973)

Alternatively, 1.6 moles of tert-butyl alcohol are added dropwise with stirring to a cooled mixture of 3.2 moles of 48 % hydrogen bromide and 100 ml of concentrated sulfuric acid at 20°C. The crude tert-butyl alcohol is separated after 30 min, washed twice with water, and dried with calcium chloride and a little calcium oxide, thus yielding 85% of tert-butyl bromide together with a little isobutene.

J. Chem. Soc, 1951, 1141

IUPAC Name

2-bromo-2-methylpropane

InChI

InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3

InChI Key

RKSOPLXZQNSWAS-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)Br

Depositor-Supplied Synonyms

2-Bromo-2-methylpropane, tert-Butyl bromide, 507-19-7, T-BUTYL BROMIDE, Trimethylbromomethane, Bromotrimethylmethane, Propane, 2-bromo-2-methyl-, 2-Bromoisobutane, 2-methyl-2-bromopropane, 1-Bromo-1,1-dimethylethane, Tertiarybutyl bromide, 2-Bromo-2-methyl-propane, NSC 8418, 1,1-Dimethylethyl bromide, 1,1-Dimethylethyl chloride, CCRIS 107, HSDB 2196, RKSOPLXZQNSWAS-UHFFFAOYSA-N, LABOTEST-BB LTBB001549, EINECS 208-065-9, SBB060197, t-butylbromide, tertbutylbromide, tert-butylbromide, tertbutyl bromide, tert. butylbromide, tert.-butylbromide, tert.butyl bromide, Butylbromide, tert-, sJPHAbIMUP@, tert-C4H9Br, PubChem3814, tertiary-butyl bromide, ACMC-209kpj, 2-bromo-2methyl-propane, AC1L1VAY, 2-Bromo-2-methyl propane, UN 2342 (Related), 2-bromanyl-2-methyl-propane, SCHEMBL22538, UNII-5LWO08435U, 135615_ALDRICH, CHEMBL347644, CTK3J4047, NSC8418, MolPort-001-768-737, WLN: EX1&1&1, 5LWO08435U, NSC-8418, STR04155, ZINC1586729, ANW-31109, STL282745, ZINC01586729, AKOS009031116, AS03433, MCULE-7499182970, RP20321, RTR-018130, TRA0008116, AN-21462, BC002616, CJ-25286, KB-68223, OR034171, DB-021214, LS-119650, TR-018130, B0617, FT-0611397, ST51046428, InChI=1/C4H9Br/c1-4(2,3)5/h1-3H, A828265, 3B4-0627, I14-0269, W-105932

Removed Synonyms

CID10485

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