1,5-Dibromopentane → 2-[6-Bromo-1-[(4-chlorophenyl)sulfonyl]hexyl]-1,4-difluorobenzene

HRID 748692Notes

Reaction equation

HRID 748692 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>O1CCCC1>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:13]([C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[S:10]([C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 81001,5-Dibromopentane2×HCID 24758Sodium hydride2×HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597509132-[6-Bromo-1-[(4-chlorophenyl)sulfonyl]hexyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 15 mg, 0.38 mmol) was added to tetrahydrofuran (10 ml). Under ice cooling, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (100 mg, 0.330 mmol) obtained in Example 5 was added. After stirring the reaction mixture at room temperature for 30 minutes, 1,5-dibromopentane (0.10 ml, 0.74 mmol) was added. The reaction mixture was stirred at room temperature for 3 days, followed by the addition of sodium hydride (60% dispersion in oil, 15 mg, 0.38 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 15 minutes and then added with 1,5-dibromopentane (0.10 ml, 0.74 mmol). The mixture was stirred at room temperature for 14 hours and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (51 mg, 30%) was obtained as a white powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 days
  2. stirringThe resulting mixture was stirred at room temperature for 15 minutes
  3. stirringThe mixture was stirred at room temperature for 14 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  7. customto yield a white solid
  8. washThe resulting white solid was washed with hexane, whereby the title compound (51 mg, 30%)
  9. customwas obtained as a white powder

Sources & evidence

ORD record
ord-0dde47eda46a4e57bcd95dc38c12fc50
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…