Carbon tetrabromide → 4-(Bromomethyl)thiophene-2-carbonitrile
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]=1Participants
5
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
- filtrationthe solution is filtered
- concentrationconcentrated
- customThe crude product is purified by column chromatography
- 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
Reaction notes
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