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

HRID 748696Notes

Reaction equation

HRID 748696 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 6344DichloromethaneSolvent2×

Procedure

The 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-4-methyl-1-pentanol (290 mg, 0.746 mmol) obtained in Example 39 and carbon tetrabromide (290 mg, 0.874 mmol) were dissolved in methylene chloride (8 ml). While stirring under ice cooling, a solution obtained by dissolving triphenylphosphine (230 mg, 0.877 mmol) in methylene chloride (2 ml) was added dropwise to the resulting solution. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 3 days. To the reaction mixture were added carbon tetrabromide (290 mg, 0.874 mmol) and triphenylphosphine (230 mg, 0.877 mmol) under ice cooling, followed by stirring 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=15:1), whereby the title compound (331 mg, 98%) was obtained as a colorless oil.

Workup

  1. customa solution obtained
  2. additionwas added dropwise to the resulting solution
  3. additionAfter completion of the dropwise addition
  4. stirringthe reaction mixture was stirred at room temperature for 3 days
  5. stirringby stirring at room temperature for 6 hours
  6. customThe residue obtained
  7. concentrationby concentrating the reaction mixture under reduced pressure
  8. customwas purified by silica gel chromatography (hexane:ethyl acetate=15:1), whereby the title compound (331 mg, 98%)
  9. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-4ef75919c7b04712924ed8e314c847ec
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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