Acetic Acid → HCID 86666826, compound

HRID 510909Notes

Reaction equation

HRID 510909 reaction equation
[F:1][C:2]1[C:3]([CH3:12])=[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]([F:1])[C:3]=1[CH3:12]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 67969214HCID 67969214, compound

Product 1

HCID 86666826HCID 86666826, compoundYield 71.6%

Procedure

To a solution of 1-(5-fluoro-2-hydroxy-4-methylphenyl)ethanone (2.2 g, 13 mmol) and acetic acid (20 mL, 400 mmol) was added N-bromosuccinimide (2.8 g, 16 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then 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, filtered and concentrated to dryness under reduced pressure. Purification on silica gel with ethyl acetate/hexanes (0-50%) gave 1-(3-Bromo-5-fluoro-2-hydroxy-4-methylphenyl)ethanone (2.3 g, 71%). 1H NMR (400 MHz, CDCl3): δ 12.80 (s, 1H), 7.40 (m, 1H), 2.60 (s, 3H), 2.40 (s, 3H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification on silica gel with ethyl acetate/hexanes (0-50%)

Sources & evidence

ORD record
ord-ce09b3f0af364e1d85460304202198dc
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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