Thionyl Chloride → 4-(Chloromethyl)-1-fluoro-2-phenoxybenzene

HRID 1110410Notes

Reaction equation

S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:3])=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of 12.6 grams (0.106 mole) of thionyl chloride and one drop (catalyst) of pyridine in 25 mL of toluene was added dropwise a solution of 19.5 grams (0.088 mole) of 4-fluoro-3-phenoxyphenylmethanol in 30 mL of toluene at such a rate as to maintain the reaction mixture temperature at 25°-35° C. Upon completion of the 45 minute addition time, the reaction mixture was warmed to 45° C. where it was stirred during a one hour period. After this time the reaction mixture was cooled, and the excess thionyl chloride was removed under reduced pressure. The residue, 23.5 grams of a semi-solid mixture, was combined with 114.2 grams of the same material from a previous reaction. The combination was distilled under reduced pressure yielding 100.3 grams of 4-fluoro-3-phenoxyphenylmethyl chloride; b.p. 98°-105° C./0.025-0.055 mm. The nmr spectrum was consistent with the proposed structure.

Workup

temperatureto maintain the reaction mixture temperature at 25°-35° C
additionUpon completion of the 45 minute addition time
temperatureAfter this time the reaction mixture was cooled
customthe excess thionyl chloride was removed under reduced pressure
customThe residue, 23.5 grams of a semi-solid mixture, was combined with 114.2 grams of the same material from a previous reaction
distillationThe combination was distilled under reduced pressure

Sources & evidence

ORD record: ord-7e6d76b1c99e421abf8572fd1deb2aea
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04975451

Reaction notes

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