Benzyl Bromide → 4-Bromo-2,6-difluoro-1-(benzyloxy)benzene

HRID 1386730

Reaction equation

HRID 1386730 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[Br:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:4]([F:9])[CH:5]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 142076414-Bromo-2,6-difluoro-1-(benzyloxy)benzeneYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g (24.0 mmol) of 2,6 difluoro-4-bromophenol in 20 ml of DMF at rt was added 5 g (36.0 mmol) of K2CO3 followed by 4.5 g (26.3 mmol) of benzyl bromide. The mixture was stirred for 12 h, diluted with H2O, the organic phase washed with sat'd NaCl, and the aqueous phase was then extracted 3× with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography with a gradient of 0-15% ethyl acetate/hexanes (v/v) afforded 6.3 g (88%) of the title compound: 1H NMR (500 MHz) δ 5.17 (s, 21), 7.06-7.11 (2H). 7.34-7.45 (5H).

Workup

  1. washthe organic phase washed with sat'd NaCl
  2. extractionthe aqueous phase was then extracted 3× with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e9b5ae7fe764c8692f1ec077e33a89d
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Linked notes

Loading…