p-Toluenesulfonic acid → 4'-Bromo-2'-fluoro-4-propyl-2,3,4,5-tetrahydro-1,1'-biphenyl

HRID 718493Notes

Reaction equation

HRID 718493 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)=[C:4]([F:18])[CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 680105851-(4-Bromo-2-fluorophenyl)-4-propylcyclohexanol

Product 1

HCID 680105864'-Bromo-2'-fluoro-4-propyl-2,3,4,5-tetrahydro-1,1'-biphenylYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A Dean-Stark condenser was attached, and a mixture of compound (68) (42.0 g, 133.2 mmol) and PTSA (0.42 g, 1 wt %) was refluxed in a toluene (300 mL) solvent for 3 hours. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and dried over magnesium sulfate. Toluene was distilled off by an evaporator, and thus 4′-bromo-2′-fluoro-4-propyl-2,3,4,5-tetrahydro-1,1′-biphenyl (69) (39.2 g, yield 99.0%) was obtained.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. distillationToluene was distilled off by an evaporator

Sources & evidence

ORD record
ord-b9d561a24da7400a9531e73e968ba076
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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