Triphenylphosphine → Methyl (3-(2-bromoethyl)benzofuran-7-yloxy)acetate
Reaction equation
O[CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>CCCCCC>[Br:38][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate (1.30 g) was dissolved in THE (15 ml) and the solution was cooled to 0° C. To this solution, triphenylphosphine (2.05 g) and N-bromosuccinimide (NBS, 1.39 g) were added and the resulting solution was stirred for 1 hour. Hexane (10 ml) was added to the reaction solution and the reaction solution was filtered through Celite. The filtrate was poured into water layer (50 ml) and extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (1.39 g, yield: 85%).
Workup
- filtrationthe reaction solution was filtered through Celite
- additionThe filtrate was poured into water layer (50 ml)
- extractionextracted twice with ethyl acetate (20 ml)
- washwashed with saturated brine
- dry with materialby drying the resultant over sodium sulfate
- customAfter removing the sodium sulfate
- filtrationby filtration
- customthe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)
Sources & evidence
- ORD record
- ord-abda48a5cade4c6fbc87a44b6168d1e8
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323235B1
Reaction notes
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