Hydrochloric Acid → 1-(3-Chloro-5-fluoro-4-methoxyphenyl)-1-hexanone

HRID 7894

Reaction equation

HRID 7894 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[O:13][CH3:14].[C:15](Cl)(=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>>[Cl:5][C:6]1[CH:11]=[C:10]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[C:8]([F:12])[C:7]=1[O:13][CH3:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 67340Hexanoyl chlorideHCID 27735812-Chloro-6-fluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 219909381-(3-Chloro-5-fluoro-4-methoxyphenyl)-1-hexanone

Procedure

Aluminum chloride (1.16 g, 8.72 mmol) was added to a stirred mixture of 1-chloro-3-fluoro-2-methoxybenzene (1.00 mL, 8.72 mmol) and hexanoyl chloride (1.47 mL, 10.46 mmol) at room temperature. The mixture warmed and HCl evolution occurred. The resulting mixture was stirred at room temperature for 67 hours and then partitioned between EtOAc (40 mL) and ice cold water (40 mL). The EtOAc layer was washed with brine (30 mL), dried over MgSO4, filtered, and evaporated under vacuum to yield crude 1-(3-chloro-5-fluoro-4-methoxyphenyl)-1-hexanone as an oil.

Workup

  1. temperatureThe mixture warmed
  2. custompartitioned between EtOAc (40 mL) and ice cold water (40 mL)
  3. washThe EtOAc layer was washed with brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-ec39dbd4e6074985880755ae6356933c
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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