Triphenylphosphine → 3-(Bromomethyl)-1-benzofuran
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.O[CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirring solution of 912 mg (3.48 mmol, 1.2 equiv) of triphenylphosphine in 5 mL of CCl4 at 0° C. is added 165 μL (3.19 mmol, 1.1 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 430 mg (2.90 mmol) of 3-hydroxymethylbenzofuran, prepared as in Intermediate 19, in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 1.5 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 20/1 as eluent afforded 500 mg of the title compound as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) δ7.71 (m, 2H), 7.50 (m, 1H), 7.37 (m, 2H), 4.62 (s, 2H); Rf =0.67 in hexane/EtOAc 5/1.
Workup
- stirringThe resulting solution is stirred 1.5 h at RT
- customthe solvent is removed in vacuo
- customPurification of the residue by silica gel flash column chromatography
Sources & evidence
- ORD record
- ord-9b3f772a1a524a8189d352fe031a8f49
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859007
Reaction notes
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