N-bromobutanimide → 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1885750Notes

Reaction equation

HRID 1885750 reaction equation
BrN1C(=O)CCC1=O.[C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:19][C:18]([CH3:21])([CH3:20])[CH2:17][CH:16](Br)[C:15]=2[CH:23]=1)#[N:10]>>[C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:19][C:18]([CH3:20])([CH3:21])[CH:17]=[CH:16][C:15]=2[CH:23]=1)#[N:10]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Procedure

The compound of the formula (II) is brominated in the benzyl position by N-bromo-succinimide in haloalkanes in the presence of a trace of peroxide and 6-cyano-3,4-dihydro-2,2-dimethyl-4-bromo-2H-1-benzopyran of the formula (X) ##STR12## is almost quantitatively formed and this can be similarly with almost quantitative yield dehydrobrominated with alkali alcoholates to produce 6-cyano-2,2-dimethyl-2H-1-benzopyran of the formula (III).

Workup

  1. customis almost quantitatively formed

Sources & evidence

ORD record
ord-40b792d5a0e74295a439935227c02789
Source dataset
uspto-grants-1992_09
Patent number
US05145985

Reaction notes

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