Benzene → 1-[(Chloromethyl)thio]-4-fluorobenzene

HRID 2050178Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C=O.[ClH:11].[CH:12]1C=CC=CC=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:12][Cl:11])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 241Benzene

HCID 313Hydrochloric Acid

HCID 712Formaldehyde

HCID 677894-Fluorothiophenol

Product 1

HCID 201613421-[(Chloromethyl)thio]-4-fluorobenzeneYield 99.8%

Procedure

This compound was prepared in the manner of Example 3.A., using 45.0 grams (0.35 mole) of a 4-fluorothiophenol, 13.5 grams (0.44 mole) of paraformaldehyde and 180 ml (1.8 moles) of concentrated hydrochloric acid in 90 ml of benzene. The residue was distilled under reduced pressure to give 61.9 grams (99.8%) of 4-fluorophenylthiomethyl chloride; b.p. 65° C./0.5 mm.

Workup

customThis compound was prepared in the manner of Example 3.A
distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record: ord-bebd06cf757248879ea4e1e2d1ff1e2e
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04200644

Reaction notes

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