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

HRID 444082Notes

Reaction equation

HRID 444082 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-ad44c049a2b543cba4bb3fed2272fe36
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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