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

HRID 989446Notes

Reaction equation

HRID 989446 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-d90804c8d3874266a8960e71e5c70b1e
Source dataset
uspto-grants-2003_10
Patent number
US06639077B2

Reaction notes

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