Methanol → Methyl 2-(3,5-difluoro-4-hydroxyphenyl)propanoate
Reaction equation
BrB(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:9]=[C:10]([F:14])[C:11]=1[O:12]C.[CH3:20]O>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([CH:15]([CH3:19])[C:16]([O:18][CH3:20])=[O:17])[CH:9]=[C:10]([F:14])[C:11]=1[OH:12]Participants
Conditions
- Temperature
- 0 °C
Procedure
tribromoborane (7.37 mL, 77.99 mmol) was added dropwise to 2-(3,5-difluoro-4-methoxyphenyl)propanoic acid (Intermediate 21-4; 2.81 g, 13.00 mmol) in dichloromethane (96 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 1 hour. The reaction mixture was added dropwise to methanol (26.3 mL, 649.92 mmol) (—care reaction is vigorous and exothermic—MeOH kept in ice bath) and the mixture was stirred for a further 20 minutes. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and washed sequentially with saturated NaHCO3 (50 mL) and water (50 mL). The organic layer was dried with MgSO4 and evaporated to afford desired product methyl 2-(3,5-difluoro-4-hydroxyphenyl)propanoate (2.490 g, 89%).
Workup
- stirringthe mixture was stirred for a further 20 minutes
- customThe reaction mixture was evaporated to dryness
- dissolutionredissolved in DCM (50 mL)
- washwashed sequentially with saturated NaHCO3 (50 mL) and water (50 mL)
- dry with materialThe organic layer was dried with MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-dd340f11b4cc4ffc99bc1a98ac4f4d77
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188092B2
Reaction notes
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