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

HRID 444073Notes

Reaction equation

HRID 444073 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1.[CH3:14][N:15](C)C=O>>[C:14]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1)#[N:15]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 162206345-Bromo-3,3-dimethylbenzofuran-2(3H)-one

Product 1

HCID 205362475-Cyano-2,3-dihydro-3,3-dimethylbenzofuran-2-oneYield 45%

Procedure

5-Bromo-2,3-dihydro-3,3-dimethylbenzofuran-2-one (39.2 g, 0.162 mole) was treated with cuprous cyanide (17.9 g, 0.2 mole) in dimethyl formamide (40 ml) (as in example 2). Recrystallisation (twice) of the product from ethanol yielded 14 g (45%) title product m.p. 138°-140° C.

Workup

  1. customRecrystallisation (twice) of the product from ethanol

Sources & evidence

ORD record
ord-929beb41ba1c4c3885132aaae178ca47
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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