Ethanol → Ethyl 4-chloro-3-(trifluoromethyl)benzoate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:20][CH3:21])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
4-Chloro-3-(trifluoromethyl)benzoic acid (1 g, 4.45 mmol) was dissolved in ethanol (3 ml) and concentrated sulfuric acid (0.15 ml) was added. The mixture was heated in the microwave at 100° C. for 5 minutes and then 120° C. for 15 minutes. The solvent was removed in vacuo and the residue partitioned between saturated aq. sodium bicarbonate (50 ml) and ethyl acetate (50 ml). The aqueous layer was extracted with further EtOAc (50 ml) and the organic phases were combined, dried with a phase separator and concentrated in vacuo to give the title compound (1.026 g) as a colourless oil. δH (methanol-d4, 400 MHz) 1.40 (3H, t), 4.41 (2H, q), 7.76 (1H, d), 8.21 (1H, dd), 8.33 (1H, d).
Workup
- customThe solvent was removed in vacuo
- customthe residue partitioned between saturated aq. sodium bicarbonate (50 ml) and ethyl acetate (50 ml)
- extractionThe aqueous layer was extracted with further EtOAc (50 ml)
- customdried with a phase separator
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9d77b407e81c476b91e4cc2af7765fb1
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324254B2
Reaction notes
Loading…