Benzoyl chloride → HCID 13956721, compound

HRID 1607361Notes

Reaction equation

HRID 1607361 reaction equation
[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([OH:13])[C:6]([Cl:12])([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]=1[CH3:30])=[O:15].[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.CCCCCC>C(OCC)C>[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([O:13][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:6]([Cl:11])([Cl:12])[C:7]([F:8])([F:10])[F:9])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]=1[CH3:30])=[O:15]

Participants

6

Reactant 4

HCID 7412Benzoyl chloride2×HCID 8058HexaneHCID 8471Triethylamine2×HCID 13933697(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxyl-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

Product 1

HCID 13956721HCID 13956721, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 390 mg (0.821 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 3, in 2 ml of diethyl ether, 0.114 ml (0.98 mmol) of benzoyl chloride and 0.137 ml of triethylamine, were added, and the mixture was stirred at room temperature for 12 hours. Then, 0.23 ml of benzoyl chloride and 0.28 ml of triethylamine were further added, and the mixture was stirred overnight at room temperature. After an addition of 5 ml of hexane, the inorganic salts are filtered off, and the filtrate was concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/1) to obtain 175 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-benzoyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationthe inorganic salts are filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/1)

Sources & evidence

ORD record
ord-6ab7d8470b5749a59fb361a7b29acb8e
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

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