1-Bromodecane → 4-Decyloxy-3-fluorophenyl bromide

HRID 2210306Notes

Reaction equation

HRID 2210306 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[F:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:2]([O:20][C:14]1[CH:15]=[CH:16][C:17]([Br:19])=[CH:18][C:13]=1[F:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 146925094-Decyloxy-3-fluorophenyl bromideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a 50 ml round bottom flask was added 2.77 g (12.5 mmoles) 1-bromodecane and 2.39 g (12.5 mmoles) 2-fluoro-4-bromophenol (1) in 25 ml methyl ethyl ketone. 4.30 g anhydrous potassium carbonate was added and the heterogeneous mixture was refluxed for 48 hrs. The reaction mixture was partitioned between ethyl ether and water, washed with brine, dried, filtered through a 2 inch plug of silica, and solvent removed to afford 4.11 g (99%) of the 4-decyloxy-3-fluorophenyl bromide (2), where R=C10H21, as a pale yellow clear oil.

Workup

  1. temperaturethe heterogeneous mixture was refluxed for 48 hrs
  2. customThe reaction mixture was partitioned between ethyl ether and water
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered through a 2 inch plug of silica, and solvent
  6. customremoved

Sources & evidence

ORD record
ord-58cfc309e21e4efd830fcb8a7edf4bbe
Source dataset
uspto-grants-1995_10
Patent number
US05457235

Reaction notes

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