Carbon tetrabromide → 5-Bromomethyl-4-chlorothiophene-3-carbonitrile

HRID 1582926Notes

Reaction equation

HRID 1582926 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[S:26][CH:25]=[C:24]([C:27]#[N:28])[C:23]=1[Cl:29].[Br:30]C(Br)(Br)Br>O1CCCC1>[Br:30][CH2:21][C:22]1[S:26][CH:25]=[C:24]([C:27]#[N:28])[C:23]=1[Cl:29]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 218665365-Hydroxymethyl-4-chlorothiophene-3-carbonitrile

Product 1

HCID 218665015-Bromomethyl-4-chlorothiophene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

36.1 g (137 mmol) of triphenylphosphine were added at 5° C. to a solution of 21.7 g (125 mmol) of 5-hydroxymethyl-4-chlorothiophene-3-carbonitrile in 250 ml of tetrahydrofuran. Then, a solution of 45.6 g (137 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was stirred overnight at room temperature. The precipitate was filtered off, the filtrate was concentrated on a rotary evaporator under a water pump vacuum, and the residue was purified by column chromatography (eluant petroleum ether:dichloromethane 1:1). This gave 26.0 g (88%) of the title compound as an oil.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated on a rotary evaporator under a water pump vacuum
  3. customthe residue was purified by column chromatography (eluant petroleum ether:dichloromethane 1:1)

Sources & evidence

ORD record
ord-c73bafda07774b0a80c60572f3879eab
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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