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

HRID 1789956Notes

Reaction equation

HRID 1789956 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-1904c867b1b84d10aefb06cd7dec1eac
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

Loading…