Thionyl Chloride → 1-(Chloromethyl)-4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzene

HRID 875344Notes

Reaction equation

HRID 875344 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:24])([F:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:3][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([F:24])([F:23])[F:5])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86709834(4-{2-[4-(Trifluoromethyl)phenyl]ethyl}phenyl)methanol

Product 1

HCID 207707551-(Chloromethyl)-4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 3.78 ml of thionyl chloride in 30 ml of dichloromethane were slowly added dropwise to a solution of 9.69 g (34.57 mmol) of (4-{2-[4-(trifluoromethyl)phenyl]ethyl}phenyl)methanol in 100 ml of dichloromethane. After the addition had ended, the reaction mixture was warmed to room temperature and stirred at this temperature for two hours. The reaction mixture was then once more cooled to 0° C., and 100 ml of saturated aqueous sodium bicarbonate solution were added slowly and carefully with vigorous stirring until a pH of 6 had been reached. The phases were then separated, and the organic phase was dried over magnesium sulphate, filtered and concentrated to dryness. This gave 8.64 g (28.92 mmol, 84% of theory) of the title compound.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then once more cooled to 0° C.
  3. stirringcarefully with vigorous stirring until a pH of 6
  4. customThe phases were then separated
  5. dry with materialthe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a1796249a81d47b29cd9c091f9c206eb
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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