Ethanol → Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].S(Cl)(Cl)=O.[CH3:17][CH2:18]O>>[CH2:17]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Br:1])[CH:3]=1)[CH3:18]Participants
4
Procedure
To a solution of 3-bromo-4-hydroxyphenylacetic acid (1.19 g, 5 mmol, 1 eq.) in EtOH (15 mL), thionyl chloride (0.73 mL, 10 mmol, 2 eq.) was added. The reaction mixture was stirred at r.t. during 1 h 30. The mixture was concentrated in vacuo. The residue was partitioned between DCM (50 mL) and sat. aq. NaHCO3 soln. (50 mL). The layers were separated and the aq. phase was extracted with DCM (2×50 mL). The comb. org. phases were dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a pale yellow oil. The product was used without further purification.
Workup
- concentrationThe mixture was concentrated in vacuo
- customThe residue was partitioned between DCM (50 mL) and sat. aq. NaHCO3 soln
- customThe layers were separated
- extractionthe aq. phase was extracted with DCM (2×50 mL)
- dry with materialphases were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-06de97c5f4c64c2ab21d02c575f825bf
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255090B2
Reaction notes
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