Ammonium Chloride → 2,2-Difluorocyclopropyl(4-chlorophenyl) ketone

HRID 561449Notes

Reaction equation

HRID 561449 reaction equation
[F:1][C:2]1([F:11])[CH2:4][CH:3]1[C:5](N(OC)C)=[O:6].Cl[Mg][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br-].[Cl-:21].[NH4+]>C1COCC1.C(OCC)C>[Cl:21][C:14]1[CH:19]=[CH:18][C:17]([C:5]([CH:3]2[CH2:4][C:2]2([F:11])[F:1])=[O:6])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 534161312,2-difluoro-N-methoxy-N-methylcyclopropane-1-carboxamideHCID 178419578HCID 178419578, compound

Product 1

HCID 248658712,2-Difluorocyclopropyl(4-chlorophenyl) ketone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.00 g (12.1 mmol) of the compound from Example 120A in 20 ml of THF was added under argon to 2.87 g (13.3 mmol) of a 1N chlorophenylmagnesium bromide solution in diethyl ether in 20 ml of THF at RT, and the mixture was heated under reflux for 2 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and extracted twice with diethyl ether, and the combined organic phases were dried over magnesium sulfate and concentrated. 2.47 g (94% of theory) of the title compound were obtained and were reacted without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionextracted twice with diethyl ether
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2dc7db6623e64040b431f836187bbf19
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…