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

HRID 1155947Notes

Reaction equation

HRID 1155947 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-0752ff598b194c4ab962419e8838d10a
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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