Carbon tetrabromide → 4-(Bromomethyl)thiophene-2-carbonitrile

HRID 2749

Reaction equation

HRID 2749 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:8]#[N:9])[S:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C1COCC1>[Br:30][CH2:2][C:3]1[CH:4]=[C:5]([C:8]#[N:9])[S:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

Product 1

HCID 107506074-(Bromomethyl)thiophene-2-carbonitrileYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-thiophene-2-carbonitrile (10 g, 72 mmol), in 360 mL of THF is added triphenyl phosphine (18.3 g, 76 mmol) and carbon tetrabromide (25 g, 76 mmol). After 3 h, the solution is filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to afford the title compound (14 g, 69 mmol) as a white solid.

Workup

  1. filtrationthe solution is filtered
  2. concentrationconcentrated
  3. customThe crude product is purified by column chromatography
  4. washeluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-3997d852565a4edcadde399de94e54e4
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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