Sodium Cyanide → (4-Bromothiophen-2-yl)acetonitrile

HRID 1082258Notes

Reaction equation

Br[CH2:2][C:3]1[S:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C-]#N.[Na+].IC1C=CC(C[C:20]#[N:21])=CC=1>>[Br:8][C:6]1[CH:7]=[C:3]([CH2:2][C:20]#[N:21])[S:4][CH:5]=1

Participants

Reactant 3

HCID 8929Sodium Cyanide

HCID 1428664-Iodophenylacetonitrile

HCID 153860154-Bromo-2-(bromomethyl)thiophene

Product 1

HCID 15386016(4-Bromothiophen-2-yl)acetonitrileYield 37%

Procedure

A mixture of the above 4-bromothiophen-2-ylmethanol (4.83 g, 25 mmol) and 63 ml of 47% hydrobromic acid was stirred vigorously for 30 minutes at room temperature. The reaction mixture was extracted with pentane to give 5.31 g (yield: 82.8%) of 2-bromomethyl-4-bromothiophene as a pale yellow oil. Thus obtained 5.12 g of 2-bromomethyl-4-bromothiophene was reacted with sodium cyanide according to the same procedure as in the synthesis of 4-iodophenylacetonitrile of example 5 to give 1.50 g (yield: 37.0%)of 4-bromothiophen-2-ylacetonitrile as a white crystal, removing by-product of α,α-bis[(4-bromothiophen-2-yl)methyl]-4-bromothiopheneaetonitrile by means of recrystalization.

Sources & evidence

ORD record: ord-f5c559616b0943af8e73f2e412636c58
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05589506

Reaction notes

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