Dimethylformamide → 5-Cyanomethyl-2,7-dibromo-3-phenylbenzofuran

HRID 1703561

Reaction equation

HRID 1703561 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([Br:19])[C:6]2[O:10][C:9]([Br:11])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:18]=1.[CH3:20][N:21](C)C=O.[C-]#N.[Na+]>O>[C:20]([CH2:2][C:3]1[CH:4]=[C:5]([Br:19])[C:6]2[O:10][C:9]([Br:11])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:18]=1)#[N:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 213199325-Bromomethyl-2,7-dibromo-3-phenylbenzofuran

Product 1

HCID 213199065-Cyanomethyl-2,7-dibromo-3-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 17.8 g. (0.040 mole) of 5-bromomethyl-2,7-dibromo-3-phenylbenzofuran in 150 ml. of N,N-dimethylformamide, 2.0 g. (0.04 mole) of sodium cyanide and 15 ml. of water is heated on a steam bath for 1.5 hours. The mixture is poured into one liter of water and stirred for about 16 hours. The mixture is extracted with 500 ml. of ethyl acetate, the extracts washed with water, then dried. Evaporation followed by trituration with hexane-ethyl acetate gives 5-cyanomethyl-2,7-dibromo-3-phenylbenzofuran as a white solid.

Workup

  1. extractionThe mixture is extracted with 500 ml
  2. washof ethyl acetate, the extracts washed with water
  3. customdried
  4. customEvaporation

Sources & evidence

ORD record
ord-2e59e37a6eea4b8e8122b05895f28d40
Source dataset
uspto-grants-1978_11
Patent number
US04124704

Linked notes

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