Thionyl Chloride → 1-(Chloromethyl)-2-(4-fluorophenoxy)benzene

HRID 2049647Notes

Reaction equation

HRID 2049647 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13]O)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[F:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][Cl:3])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 3700253HCID 3700253, compound

Product 1

HCID 203438271-(Chloromethyl)-2-(4-fluorophenoxy)benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

8.5 g of thionyl chloride are added dropwise over a 10 minutes span to a stirring mixture of 13.0 g of 2-(4-fluorophenoxy)benzyl alcohol in 80 ml of benzene at ambient temperature. After total addition, the reaction mixture is stirred for 16 hours before being carefully poured onto 350 ml of crushed ice containing 8 ml of sodium bicarbonate. The mixture is stirred until the ice melts. The layers separate and the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution, washed twice with 40 ml portions of water, washed once with a 25 ml portion of a saturated sodium chloride solution, dried and rotary evaporated to provide a clear liquid. The liquid is distilled at 106°-109° C. and 0.16 mm to provide a clear colorless liquid of 2-(4-fluorophenoxy)benzyl chloride.

Workup

  1. additionAfter total addition
  2. customThe layers separate
  3. washthe benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution
  4. washwashed twice with 40 ml portions of water
  5. washwashed once with a 25 ml portion of a saturated sodium chloride solution
  6. customdried
  7. customrotary evaporated
  8. customto provide a clear liquid
  9. distillationThe liquid is distilled at 106°-109° C.

Sources & evidence

ORD record
ord-c4d013f87d784d7dba26ac0afe834a9a
Source dataset
uspto-grants-1980_04
Patent number
US04198418

Reaction notes

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