Thionyl Chloride → 4-(4-Trifluoromethylbenzyloxy)-2-chloromethylpyridine

HRID 1196623Notes

Reaction equation

HRID 1196623 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH2:15]O)[CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:23])=O>ClCCl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][Cl:23])[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 144259724-(4-Trifluoromethylbenzyloxy)-2-hydroxymethylpyridine

Product 1

HCID 144259864-(4-Trifluoromethylbenzyloxy)-2-chloromethylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.2 g (7.8 mmol) of the title compound from Example 3 are dissolved in 50 ml of anhydrous dichloromethane and a solution of 2 ml of thionyl chloride in 6 ml of dichloromethane is added dropwise at -10° C. The mixture is warmed to room temperature, stirred for 30 minutes more, and concentrated. The crystalline residue is brought to crystallization using diisopropyl ether and dried using an oilpump, m.p. 133°-135° C.

Workup

  1. concentrationconcentrated
  2. customThe crystalline residue is brought to crystallization
  3. customdried

Sources & evidence

ORD record
ord-a9a3fc14b80044d4ada986a19f0862a4
Source dataset
uspto-grants-1992_05
Patent number
US05114955

Reaction notes

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