Thionyl Chloride → 1-(Chloromethyl)-4-[2-(4-fluorophenyl)ethyl]benzene

HRID 875335Notes

Reaction equation

HRID 875335 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:3][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate2×HCID 86709824{4-[2-(4-Fluorophenyl)ethyl]phenyl}methanol

Product 1

HCID 220150131-(Chloromethyl)-4-[2-(4-fluorophenyl)ethyl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 14.96 ml of thionyl chloride in 100 ml of dichloromethane were slowly added dropwise to a solution of 31.5 g (136.7 mmol) of {4-[2-(4-fluorophenyl)ethyl]phenyl}methanol in 400 ml of dichloromethane. After the addition had ended, the reaction mixture was warmed to room temperature and stirred at this temperature for another 2 hours. The reaction mixture was then once more cooled to 0° C., and 200 ml of saturated aqueous sodium bicarbonate solution were added slowly and carefully, with vigorous stirring. Subsequently, small portions of solid sodium bicarbonate were added to the solution until the pH had been adjusted to 6. The phases were then separated, and the organic phase was dried over magnesium sulphate, filtered and concentrated to dryness. This gave 28.5 g (114.5 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. customThe phases were then separated
  4. dry with materialthe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e911f3f4d2824096948a971de7149160
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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