Water → 1-(Benzyloxy)-2-chloro-3-nitrobenzene

HRID 1886980Notes

Reaction equation

HRID 1886980 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Cl:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 3013917Phenol, 2-chloro-3-nitro-

Product 1

HCID 143561211-(Benzyloxy)-2-chloro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5.37 g (30.9 mmol) of 2-chloro-3-nitrophenol and 12.6 g (38.7 mmol) of cesium carbonate in 60 mL of dimethylformamide (DMF) was cooled to 0° C. and 4.04 mL (34.0 mmol) of benzyl bromide was added. The mixture was warmed to 22° C. and stirred for 16 hours. Water was added and the resulting mixture was extracted with ether. The organic extract was dried (Na2SO4) and evaporated. The residue was crystallized from ethyl acetate and hexane to give 1-(benzyloxy)-2-chloro-3-nitrobenzene.

Workup

  1. temperatureThe mixture was warmed to 22° C.
  2. extractionthe resulting mixture was extracted with ether
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated
  6. customThe residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-493ff34e60c14238a601e5d8499ab7f5
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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