Dimethylformamide → 5-Cyano-2,3-dihydro-3,3-dimethylbenzofuran

HRID 1155956Notes

Reaction equation

HRID 1155956 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[CH3:13][N:14](C)C=O>>[C:13]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1)#[N:14]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 205361905-Cyano-2,3-dihydro-3,3-dimethylbenzofuran

Procedure

5-Bromo-2,3-dihydro-3,3-dimethylbenzofuran (15 g, 0.066 mole) was heated under reflux with cuprous cyanide (7.2 g, 0.08 mole) in dimethyl formamide (15 ml) as in Example 2. Work up yielded, after recrystallisation from petroleum ether (bp 60°-80° C.) with charcoaling, 5.7 g of product, mp 72°-75° C.

Workup

  1. customWork up yielded
  2. customafter recrystallisation from petroleum ether (bp 60°-80° C.) with charcoaling, 5.7 g of product, mp 72°-75° C.

Sources & evidence

ORD record
ord-c82f93d08ea64243962a22e32b72a3d9
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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