Chlorodifluoromethane → HCID 67465272, compound

HRID 2171162Notes

Reaction equation

HRID 2171162 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH2:12][O:13][CH3:14])=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:22]([F:24])[F:23]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:22]([F:24])[F:23])[C:3]=1[O:11][CH2:12][O:13][CH3:14]

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 67466846HCID 67466846, compound

Product 1

HCID 67465272HCID 67465272, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-45 °C

Procedure

To a stirring solution of 3-bromo-6-methoxy-2-(methoxymethoxy)phenol (700 mg, 2.64 mmol) in dimethylformamide (15 mL) was added potassium carbonate (729 mg, 5.28 mmol), cooled to −45° C. and chlorodifluoromethane gas was passed for 10 min and the resultant reaction mixture was heated to 80° C. for 2 h. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-5% ethyl acetate in pet ether) afforded 1-Bromo-3-(difluoromethoxy)-4-methoxy-2-(methoxymethoxy)benzene as a liquid (250 mg, 30%).

Workup

  1. customthe resultant reaction mixture
  2. temperaturewas heated to 80° C. for 2 h
  3. customThe reaction mixture was quenched with ice-cold water
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by flash column chromatography (silica gel, 0-5% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-d701b2f4c9d94a509c79338da2fa40ba
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…