N-bromobutanimide → 1-(3-Bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone

HRID 510998Notes

Reaction equation

HRID 510998 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.[Br:13]N1C(=O)CCC1=O>C(O)(=O)C>[Br:13][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

Reactant 2

HCID 67184N-bromobutanimideHCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

Product 1

HCID 866668921-(3-Bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanoneYield 93.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-(5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (8.0 g, 42 mmol) in acetic acid (80 mL) was added N-bromosuccinimide (9.0 g, 50 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated, neutralized with saturated sodium bicarbonate solution and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and then concentrated to dryness under reduced pressure. The residue was purified on silica gel, eluting with 0 to 20% EtOAc in hexane, to yield the desired product (10.5 g, 93%). LCMS calculated for C8H6BrClFO2 (M+H)+: m/z=266.9, 268.9. found: 267.1, 269.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 20% EtOAc in hexane

Sources & evidence

ORD record
ord-98f2fe218fea455680002043f7f36136
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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