Phenol → 4-Chloro-1-(2-hydroxyphenyl)butan-1-one

HRID 50983Notes

Reaction equation

HRID 50983 reaction equation
B(F)(F)F.CCOCC.[F:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>>[Cl:25][CH2:26][CH2:27][CH2:28][C:29]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][C:13]=1[OH:17])=[O:30].[Cl:25][CH2:26][CH2:27][CH2:28][C:29]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[OH:24])=[O:30]

Participants

6

Reactant 4

HCID 996PhenolHCID 8000Boron trifluoride etherateHCID 97433-FluorophenolHCID 783704-Chlorobutyryl chloride

Product 2

HCID 108673114-Chloro-1-(2-hydroxyphenyl)butan-1-oneHCID 147738734-Chloro-1-(4-fluoro-2-hydroxyphenyl)butan-1-one

Conditions

Temperature
130 °C

Procedure

To a cold boron trifluoride etherate (280 mmol) solution was added 3-Fluorophenol or phenol (89 mmol) and 4-chlorobutyryl chloride (178 mmol). The resulting solution was stirred at 130° C. for 18 hours. The reaction mixture was cooled and poured into ice water (100 mL). After stirring for 10 minutes, the water mixture was extracted with ether (3×100 mL). The ether layer was washed with brine (100 mL), dried over MgSO4, filtered and concentrated to a residue to afford 4-chloro-1-(4-fluoro-2-hydroxyphenyl)butan-1-one and 4-chloro-1-(2-hydroxyphenyl)butan-1-one in 52%-67% yield, which was used in the following step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringAfter stirring for 10 minutes
  3. extractionthe water mixture was extracted with ether (3×100 mL)
  4. washThe ether layer was washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-027a4a3c215c4fc281779d0ff50e2be1
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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