Benzyl Chloride → 4-(Benzyloxy)-1-bromo-2-(trifluoromethoxy)benzene

HRID 1027238Notes

Reaction equation

HRID 1027238 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][C:10]([F:12])([F:11])[F:13])[CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 177507434-Bromo-3-(trifluoromethoxy)phenol

Product 1

HCID 672362364-(Benzyloxy)-1-bromo-2-(trifluoromethoxy)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-bromo-3-(trifluoromethoxy)phenol (2.97 g, 11.6 mmol) in DMF (10 mL) was added Cs2CO3 (5.65 g, 17.3 mmol) and benzyl chloride (1.46 mL, 12.7 mmol) at RT. The reaction mixture was stirred overnight then quenched with water and diluted with EtOAc. The organic phase was washed with water (3×), brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/Heptane) to afford the title compound as a colorless oil (3.92 g, 98% yield). 1H NMR (METHANOL-d4) δ 7.51 (d, J=9.1 Hz, 1H), 7.40-7.45 (m, 4H), 7.34-7.40 (m, 1H), 6.97 (dd, J=2.5, 1.5 Hz, 1H), 6.82 (dd, J=9.1, 3.0 Hz, 1H), 5.06 (s, 2H).

Workup

  1. customthen quenched with water
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (EtOAc/Heptane)

Sources & evidence

ORD record
ord-a6f5d0dcec7c479093d8bf9600e3f85b
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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