Benzyl Alcohol → 1-(Benzyloxy)-3-bromo-5-fluorobenzene

HRID 709680Notes

Reaction equation

HRID 709680 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14](F)[CH:13]=1.O>C1COCC1>[CH2:1]([O:8][C:14]1[CH:15]=[C:16]([F:18])[CH:17]=[C:12]([Br:11])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneYield 137.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl alcohol (1.10 g) in THF (90 mL) was added 60% sodium hydride (2.50 g) at 0° C., and the mixture was stirred for 1 hr. A solution of 1-bromo-3,5-difluorobenzene (1.00 g) in THF (10 mL) was added dropwise to the reaction mixture at 0° C. over 1 hr, and the mixture was stirred for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.00 g) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-50f5ae073985464393776ea8f30aef34
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…