2-Chloro-1,1,1-trifluoroethane → Benzyl 2,2,2-trifluoroethyl sulfide

HRID 256763

Reaction equation

Cl[CH2:2][C:3]([F:6])([F:5])[F:4].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC>[F:4][C:3]([F:6])([F:5])[CH2:2][S:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-chloro-2,2,2-trifluoroethane (20 g), benzyl mercaptan (12.4 g, 99% strength), sodium hydroxide (22.0 g of a 22% aqueous solution) and hexadecyl tributyl phosphonium bromide (0.51 g) was charged to a resealable Carius tube under a nitrogen atmosphere and heated at 70° C. for 10 hours. The tube was then cooled to 0° C., unsealed and the contents separated into two layers. The lower organic layer was collected, washed with water and purified by short path distillation to give 2,2,2-trifluoroethylthiomethylbenzene, b.p. 60°-70° C./ 10 mmHg, 17.4 g (yield 84%, strength 99%). The identity of the product was confirmed by gc-mass spectroscopy and nuclear magnetic reconance, and by comparison with data provided in C. Bunyagidj et al, J Org. Chem., 1981, 46 3335.

Workup

additionwas charged to a resealable Carius tube under a nitrogen atmosphere
temperatureThe tube was then cooled to 0° C.
customunsealed and the contents separated into two layers
customThe lower organic layer was collected
washwashed with water
distillationpurified by short path distillation

Sources & evidence

ORD record: ord-3a7efd3878424318b295329d78bcf8e4
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258547

Linked notes

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