1-Bromopentane → 1,2-Difluoro-3-(4-pentyloxybutoxy)benzene

HRID 6590

Reaction equation

HRID 6590 reaction equation
[H-].[Na+].[F:3][C:4]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C>[F:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=1[F:3]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 220162574-(2,3-Difluorophenoxy)-butan-1-ol

Product 1

HCID 220162621,2-Difluoro-3-(4-pentyloxybutoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1 equi.) was added to the solution of 4-(2,3-difluorophenoxy)-butan-1-ol (22), (1 equi.) and 1-bromopentane (1 equi.) in DMF (1 mL/mmole) and the reaction mixture was stirred at room temperature for 12 h,. quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), as a white solid (84%).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane (1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography
  7. customon silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-ed18f3b23e5b4b238c3b0edae8dd78e6
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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