Sodium Carbonate → 1-(3-Fluoro-4-hydroxyphenyl)propan-1-one

HRID 626139Notes

Reaction equation

HRID 626139 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[O:8]C.C([O-])([O-])=O.[Na+].[Na+]>Br>[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 2762841-(3-Fluoro-4-methoxyphenyl)propan-1-one

Product 1

HCID 133224411-(3-Fluoro-4-hydroxyphenyl)propan-1-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-(3-Fluoro-4-methoxyphenyl)propan-1-one (421 mg, 2.31 mmol) in 20 mL 40% HBr was refluxed for 1 h., neutralized with solid Na2CO3 at 0° C., and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography (eluent: petroleum ether/EtOAc=5/1) over silica gel to give the product (257 mg, 66% yield) as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography (eluent: petroleum ether/EtOAc=5/1) over silica gel

Sources & evidence

ORD record
ord-bf31d5c70c364868882031a15011a248
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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