Carbon tetrabromide → 3-(Bromomethyl)thiophene-2-carbonitrile
Reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH2:8]O)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]C(Br)(Br)Br>C1COCC1>[Br:29][CH2:8][C:7]1[CH:6]=[CH:5][S:4][C:3]=1[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
11.7 g (84.07 mmol) of 2-cyano-3-hydroxymethylthiophene were dissolved together with 24.1 g (91.87 mmol) of triphenylphosphine in 100 ml of THF at room temperature and, while cooling (ice bath), 30.47 g (91.87 mmol) of tetrabromomethane were added in portions. Stirring at room temperature for 3 hours was followed by concentration under reduced pressure and purification by chromatography on silica gel (methylene chloride/petroleum ether) to result in 18.8 g of pale yellow crystalline product still containing petroleum ether.
Workup
- additionwere added in portions
- concentrationwas followed by concentration under reduced pressure and purification by chromatography on silica gel (methylene chloride/petroleum ether)
Sources & evidence
- ORD record
- ord-b32d28022c9e48baae1e8c8dfc583868
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114358
Reaction notes
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