1-Bromo-2-Chloroethane → HCID 22598010, compound

HRID 2184959Notes

Reaction equation

HRID 2184959 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12])[CH:5]=[O:6].Br[CH2:15][CH2:16][Cl:17].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:12])[F:13])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 22598010HCID 22598010, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-hydroxy-4-difluoromethoxybenzaldehyde (77 g, 409 mmol), 1-bromo-2-chloroethane (176 g, 1.23 mol) and Cs2CO3 (146 g, 449 mmol) in DMF (2 L) was stirred at 70° C. for 3 h and at 55° C. for 15 h. The mixture was cooled to room temperature and partitioned between ethyl acetate (1 L) and water (2 L). The aqueous layer was extracted with ethyl acetate (2×) and the combined organics were washed with water, dried (Na2SO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/ethyl acetate 4:1 to 7:3) provided the 3-(2-Chloro)ethoxy-4-difluoromethoxybenzaldehyde compound (87 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (1 L) and water (2 L)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  4. washthe combined organics were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25f2d48d677149a1900ccf8f09798202
Source dataset
uspto-grants-2002_06
Patent number
US06399636B2

Reaction notes

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