Synthesis of bromobenzyl cyanide

Preparation of bromobenzyl cyanide

Bromobenzyl cyanide is prepared from benzyl bromide by converting to benzyl cyanide, which is afterwards brominated.

Preparation of bromobenzyl cyanide

Preparation of bromobenzyl cyanide

To the round bottom flask fitted with a reflux condenser 60 g benzyl bromide, 27 g potassium cyanide, 45 g ethyl alcohol and 25 g water are placed. The reaction mixture is refluxed for 4 hours, then extracted with ether, the ether extract separated and dried over calcium chloride, the ether distilled off. Benzyl cyanide distilled, the fraction passing over between 210° and 240° C is collected. Additional distillation and collection fraction boiling between 228° and 233° C yields 36 g benzyl cyanide.

To the round bottom flask fitted with a reflux condenser and dropping funnel 36 g benzyl cyanide are placed. The top of the condenser is connected with a flask containing water (for absorption of hydrobromic acid evolved during the reaction). 60 g bromine are added slowly from the dropping-funnel during 30 min while the benzyl cyanide is heated to 120° C. After allowing the reaction mixture to cool, bromobenzyl cyanide is washed with 5% sodium carbonate solution, extracted with ether and dried with calcium chloride, filtered and the ether removed by distillation. The residue is then distilled in steam or at reduced pressure at 25 mm of Hg. Bromobenzyl cyanide forms yellowish-white crystals with melting point 25.4° C and boiling point at 242° C.

The war gases chemistry and analysis, by M. Sartory, 196-197, 1939.

IUPAC Name

2-bromo-2-phenylacetonitrile

InChI

InChI=1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H

InChI Key

XUHFBOUSHUEAQZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C#N)Br

Depositor-Supplied Synonyms

Bromobenzyl cyanide, 5798-79-8, 2-bromo-2-phenylacetonitrile, Brombenzyl cyanide, Bromo(phenyl)acetonitrile, Camite, Bromobenzylcyanide, Bromobenzylnitrile, alpha-Bromophenylacetonitrile, alpha-Bromobenzeneacetonitrile, CA (Tear gas), Acetonitrile, bromophenyl-, alpha-Bromo-alpha-tolunitrile, alpha-Brombenzylkyanid [Czech], ALPHA-BROMOBENZYL CYANIDE, CHEMBL1085832, HSDB 1982, Benzeneacetonitrile, alpha-bromo-, Acetic acid, bromophenyl-, nitrile, EINECS 227-348-8, SBB061313, BRN 1862309, 2-bromo-2-phenylethanenitrile, cyanobenzyl bromide, bromo benzyl cyanide, alpha-Brombenzylkyanid, AC1L2JMW, Benzeneacetonitrile, a-bromo-, SCHEMBL437646, CTK8C5267, MolPort-001-781-521, XUHFBOUSHUEAQZ-UHFFFAOYSA-N, ANW-74981, AKOS005146417, RP25404, VZ23904, Benzeneacetonitrile, alpha-bromo- (9CI), AK-48357, AM806881, BC620262, BR-48357, KB-21121, LS-13220, SC-45500, (S)-alpha-Bromo-alpha-phenyl acetonitrile, DB-029546, TC-163726, FT-0083469, FT-0651446, ST51047338, W7126, A18929, S-6567, 3-09-00-02278 (Beilstein Handbook Reference), S01-0406

Removed Synonyms

.alpha.-Bromobenzyl cyanide, CID22044, Benzeneacetonitrile, .alpha.-bromo-, BBC, BBN, CA

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