Ammonium Chloride → 1-(2-(4-Fluorophenylthio)-6-fluorophenyl)prop-2-en-1-ol

HRID 1974758Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:10]=2[CH:11]=[O:12])=[CH:4][CH:3]=1.[CH:18]([Mg]Br)=[CH2:19].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:10]=2[CH:11]([OH:12])[CH:18]=[CH2:19])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(4-fluorophenylthio)-6-fluorobenzaldehyde (2.06 g, 8.23 mmol) is dissolved in 21 ml of dry THF and cooled to -78° C. Vinylmagnesium bromide solution (12.4 ml of a 1.0M solution in THF) is then added dropwise and the reaction mixture is allowed to warm to room temperature. The reaction mixture is then poured into saturated NH4Cl and extracted twice with diethyl ether. The extracts are washed with water and then brine and dried over K2CO3 to afford the subtitle compound.

Workup

temperatureto warm to room temperature
extractionextracted twice with diethyl ether
washThe extracts are washed with water
dry with materialbrine and dried over K2CO3

Sources & evidence

ORD record: ord-c014643ec5124cdba8c29893dad98860
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283361

Reaction notes

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