Methanol → Methyl (4-bromo-2-fluorophenyl)acetate
Reaction equation
C[OH:2].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([F:13])[CH:5]=1.O.[C:15]([O-])([O-])=[O:16].[Na+].[Na+]>C(Cl)Cl>[CH3:15][O:16][C:11](=[O:2])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][C:6]=1[F:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
MeOH (16 mmol, 0.81 ml), TMSCI (20 mmol, 2.13 g) and (4-bromo-2-fluorophenyl) acetonitrile (10 mmol, 2.13 g) were sequentially added to a dry flask under a nitrogen atmosphere at room temperature. The reaction mixture was heated at 50° C. for 4 hours. After being cooled to room temperature, water (20 mmol, 0.36 ml) was added to the mixture, followed by the addition of Na2CO3 (10 mmol, 1.06 g) and CH2Cl2 (10 ml). Drying over MgSO4 and concentrating at low pressure afforded product (0.85 g, 35% yield). 1H NMR (300 MHz, CDCl3) δ: 3.57 (s, 2 H), 3.65 (s, 3H), 7.08 (t, J=8.3 Hz, 1H), 7.16–7.21 (m, 2H).
Workup
- temperatureAfter being cooled to room temperature
- dry with materialDrying over MgSO4
- concentrationconcentrating at low pressure
Sources & evidence
- ORD record
- ord-061d45dc4ee942bda20dce12ba5fa327
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148226B2
Reaction notes
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