Methanol → Methyl 4-(1-bromoethyl)benzoate
Reaction equation
[Br:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[CH3:13]O>C1COCC1>[Br:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=1)[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A solution of trimethylsillyldiazomethane in THF (2M, 49.1 mL, 98.3 mmol) was added dropwise to a solution of 4-(1-bromoethyl)benzoic acid (15 g, 66 mmol) in methanol (75 mL) and THF (75 mL) at 0° C. The resulting mixture was stirred at 23° C. for 3 h, then concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (2×). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.02 (d, 2H, J=8.5 Hz), 7.51 (d, 2H, J=8.2 Hz), 5.21 (q, 1H, J=6.7 Hz), 3.92 (s, 3H), 2.06 (d, 3H, J=7.0 Hz).
Workup
- concentrationconcentrated
- custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (2×)
- washThe combined organic layers were washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c1c94009349a4466afb3e5693c454139
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296750B2
Reaction notes
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