1,4-Dibromobutane → N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841597Notes

Reaction equation

HRID 1841597 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23446603N-(4-hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 23446540N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.63 g (20 mmol) of N-(4-Hydroxy-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide in 150 ml of DMF was treated with 7.1 ml (60 mmol) of 1,4-dibromobutane and with 1.00 g (23 mmol) of 55% NaH (in small portions) at 0° C. The reaction mixture was stirred for 4 h at RT, poured into cooled aqueous saturated NH4Cl and extracted (Et2O 3×). The organic phase was washed with aqueous 10% NaCl, dried (NaSO4) evaporated and purified by flash silica gel column (first with hexane to remove the dibromobutane and then Hexane/EtOAc 95:5) to yield 7.7 g (83%) of N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, mp: 91-92° C.; MS: 465 (M, 1 Br).

Workup

  1. additionpoured
  2. extractionextracted (Et2O 3×)
  3. washThe organic phase was washed with aqueous 10% NaCl
  4. dry with materialdried (NaSO4)
  5. customevaporated
  6. custompurified by flash silica gel column (first with hexane
  7. customto remove the dibromobutane

Sources & evidence

ORD record
ord-32f9a48d56e748fd9a9e7d04fca22d57
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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