Phenol → 4-Bromo-1-chloro-2-(phenoxymethyl)benzene

HRID 1474593Notes

Reaction equation

HRID 1474593 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9]Cl)[CH:3]=1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 433790704-Bromo-1-chloro-2-(chloromethyl)benzene

Product 1

HCID 115149114-Bromo-1-chloro-2-(phenoxymethyl)benzeneYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-1-chloro-2-(chloromethyl)benzene (12.2 g, 50.85 mmol) and phenol (4.79 g, 50.85 mmol) in DMF (102 mL) under nitrogen atmosphere, K2CO3 was added (35.14 g, 254.25 mmol). The resulting mixture was stirred at r.t. for 18 h. After completion of the reaction as confirmed by TLC, the reaction mixture was passed through celite plug and the filterate was evaporated. The residue obtained was dissolved in ethyl acetate (100 mL) and washed with water (2×100 mL) and brine (2×100 mL) successively. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1:9 Ethyl acetate:Pet. Ether) to afford the title compound (14.7 g, 97.3%).

Workup

  1. customAfter completion of the reaction
  2. customthe filterate was evaporated
  3. customThe residue obtained
  4. washwashed with water (2×100 mL) and brine (2×100 mL) successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford crude product which
  8. customwas purified by column chromatography (silica gel, 1:9 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-f91be53191744b759418a952941ac6f5
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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