Acetic Acid → 1-(3-Bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone
Reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(O)(=O)C.[Br:17]N1C(=O)CCC1=O>>[Br:17][C:4]1[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[F:12]Participants
4
Procedure
To a stirred solution of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (7.9 g, 42 mmol) in acetic acid (80 mL, 1.0 mol) was added N-bromosuccinimide (9.0 g, 50 mmol) and the resulting mixture was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo, neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to dryness under reduced pressure. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to yield the desired product (93% yield). 1H NMR (300 MHz, CDCl3): δ 13.15 (s, 1H), 7.79 (m, 1H), 2.62 (s, 3H).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness under reduced pressure
- customThe residue was purified on silica gel
- washeluting with 0 to 20% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-b0a2dee4d9794264a99ff01ae3d92b5c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126948B2
Reaction notes
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