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

HRID 262092

Reaction equation

HRID 262092 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-c3db855a9ec247f7b025540825bc0a75
Source dataset
uspto-grants-1979_05
Patent number
US04153619

Linked notes

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