Methanol → methyl 2-bromo-2-(3-bromophenyl)acetate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]C(O)=O)[CH:5]=[CH:6][CH:7]=1.P(Br)(Br)[Br:13].BrBr.[CH3:18][OH:19].CC[O:22][CH2:23]C>>[Br:13][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:18]([O:22][CH3:23])=[O:19]Participants
6
Procedure
To 3-bromophenylacetic acid (10 g, 47 mmol) under argon was added PBr3 (11.2 mL, 118 mmol) and the suspension stirred at room temperature for 45 minutes. Bromine (11.1 mL, 216 mmol) was added dropwise over 5 minutes. The mixture was stirred at 100° C. for 3 hours and then cooled. Anhydrous methanol (35 mL) was added dropwise over 30 minutes, and then the reaction mixture was diluted with ether (400 mL), washed with 5% NaHCO3 (800 mL), brine (200 mL), and then dried over MgSO4. The mixture was filtered and concentrated in vacuo to afford material of sufficient purity to use directly.
Workup
- stirringThe mixture was stirred at 100° C. for 3 hours
- temperaturecooled
- washwashed with 5% NaHCO3 (800 mL), brine (200 mL)
- dry with materialdried over MgSO4
- filtrationThe mixture was filtered
- concentrationconcentrated in vacuo
- customto afford material of sufficient purity
Sources & evidence
- ORD record
- ord-8d88036002e8427d92f6a13cc5bfb699
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06509335B1
Reaction notes
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