Pyridine → 1-Chloro-4-{[2-(chloromethyl)phenyl]sulfanyl}-2-methoxybenzene

HRID 1732771Notes

Reaction equation

HRID 1732771 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15]O)=[CH:8][C:7]=1[O:21][CH3:22].N1C=CC=CC=1>O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][Cl:3])=[CH:8][C:7]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12374605{2-[(4-Chloro-3-methoxyphenyl)sulfanyl]phenyl}methanol

Product 1

HCID 123746081-Chloro-4-{[2-(chloromethyl)phenyl]sulfanyl}-2-methoxybenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (6.5 g) is added dropwise to a stirred mixture of the alcohol from the preceding preparation (11.2 g) and pyridine (4.0 g) at 10°-20° C. The mixture is stirred at room temperature for 3 hours and, after standing overnight, for one additional hour at 30°-40° C. The cooled mixture is decomposed by dropwise addition of water (20 ml) and the product extracted with benzene. The work-up of the extract, followed by crystallization of the crude residue from a small volume of hexane, yields 10.2 g (85%) of 2-(4-chloro-3-methoxyphenylthio)benzyl chloride which in the pure state melts at 57°-59° C.

Workup

  1. waitafter standing overnight, for one additional hour at 30°-40° C
  2. extractionthe product extracted with benzene
  3. customThe work-up of the extract, followed by crystallization of the crude residue from a small volume of hexane

Sources & evidence

ORD record
ord-0f3014e39cd84df6a31391a9025240a1
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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