1,6-Dibromohexane → {4-((6-Bromohexyl)oxy]-3,3-difluorobutyl}benzene

HRID 1966616Notes

Reaction equation

HRID 1966616 reaction equation
[F:1][C:2]([F:13])([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:4].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:4][CH2:3][C:2]([F:13])([F:1])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 184257752,2-Difluoro-4-phenylbutan-1-ol

Product 1

HCID 67246468{4-((6-Bromohexyl)oxy]-3,3-difluorobutyl}benzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolvent

Procedure

To a solution of Intermediate 2 (0.60 g, 3.22 mmol) in 1,6-dibromohexane (1.74 mL, 11.27 mmol) was added tetrabutylammonium bromide (21 mg, 0.064 mmol) and 50% sodium hydroxide (1.2 mL). The mixture was stirred at room temperature overnight. The crude reaction was diluted with n-hexane (20 mL), washed with water (2×10 mL), dried (Na2SO4), and the solvent removed under reduced pressure. The title compound was obtained (2.1 g, 52% purity) and was used in the next step without further purification.

Workup

  1. customThe crude reaction
  2. washwashed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-63e232ace87f41cc849e4b84569ba0dc
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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