Methanol → Methyl 2-(2-bromophenyl)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]Participants
4
Conditions
- Temperature
- 62.5 °C
Procedure
Combine 2-bromophenylacetic acid (500.0 g, 2.33 mol) with methanol (5.0 L) under a nitrogen atmosphere. Add concentrated sulfuric acid (185.8 mL) drop-wise at 20-35° C., and then warm to 60-65° C. with stirring for 3-4 hours. Cool the reaction mixture to 45° C. and concentrate under reduced pressure below 45° C. to a volume of approximately 750 mL. Cool the reaction mixture to 10-30° C. and add dichloromethane (2.5 L). Adjust the pH to 7-8 with sodium hydroxide (7%, 380.0 mL) and separate the layers. Concentrate the organic phase to dryness under reduced pressure below 45° C. to obtain the title compound (516.5 g, 97.0%) as a yellow oil.
Workup
- temperatureCool the reaction mixture to 45° C.
- concentrationconcentrate under reduced pressure below 45° C. to a volume of approximately 750 mL
- temperatureCool the reaction mixture to 10-30° C.
- additionadd dichloromethane (2.5 L)
- customseparate the layers
- concentrationConcentrate the organic phase to dryness under reduced pressure below 45° C.
Sources & evidence
- ORD record
- ord-d213c0394bcc4960b9c2e83d9b12646d
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569286B2
Reaction notes
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