Carbon tetrabromide → 2-[5-Bromo-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene

HRID 748697Notes

Reaction equation

HRID 748697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH:12]([CH3:17])[CH2:13][CH2:14][CH2:15]O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:27][CH2:15][CH2:14][CH2:13][CH:12]([CH3:17])[CH:11]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[F:25])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 597508955-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol

Product 1

HCID 597507782-[5-Bromo-1-[(4-chlorophenyl)sulfonyl]-2-methylpentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol (170 mg, 0.437 mmol) obtained in Example 40 and carbon tetrabromide (170 mg, 0.648 mmol) were dissolved in methylene chloride (8 ml). While stirring under ice cooling, triphenylphosphine (135 mg, 0.515 mmol) was added to the resulting solution, followed by stirring at room temperature for 14 hours. To the reaction mixture were added carbon tetrabromide (170 mg, 0.437 mmol) and triphenylphosphine (135 mg, 0.515 mmol) under ice cooling. The reaction mixture was stirred at room temperature for 6 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=10:1), whereby the title compound (192 mg, 97%) was obtained as a colorless oil.

Workup

  1. stirringby stirring at room temperature for 14 hours
  2. stirringThe reaction mixture was stirred at room temperature for 6 hours
  3. customThe residue obtained
  4. concentrationby concentrating the reaction mixture under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=10:1), whereby the title compound (192 mg, 97%)
  6. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-fd886f49bd004dcaba70aa3e39e60610
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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