Hydrogen Bromide → 1-[2-(4-Fluorophenylthio)-6-fluorophenyl]3-bromoprop-1-ene

HRID 1974759Notes

Reaction equation

HRID 1974759 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[CH:16](O)[CH:17]=[CH2:18])=[CH:4][CH:3]=1.C(OCC)C.[BrH:25].O>CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[CH:16]=[CH:17][CH2:18][Br:25])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 3283Diethyl EtherHCID 191022051-(2-(4-Fluorophenylthio)-6-fluorophenyl)prop-2-en-1-ol

Product 1

HCID 540068731-[2-(4-Fluorophenylthio)-6-fluorophenyl]3-bromoprop-1-ene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1-(2-(4-fluorophenylthio)-6-fluorophenyl)prop-2-en-1-ol (2.29 g, 8.23 mmol) is dissolved in 10 ml of hexane and 10 ml of diethyl ether and cooled in an ice bath. Concentrated HBr acid (4.6 ml, 41.2 mmol) is then added dropwise and the reaction mixture is stirred vigorously for 5 hours at room temperature. The reaction mixture is then poured into water and extracted twice with diethyl ether. The extracts are washed with water and then brine and dried over MgSO4 to afford the subtitle compound.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe extracts are washed with water
  3. dry with materialbrine and dried over MgSO4

Sources & evidence

ORD record
ord-51a5f4a8e8dc4914ada856c72ccb657d
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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