Hydrochloric Acid → HCID 67466666, compound

HRID 2171173Notes

Reaction equation

HRID 2171173 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[C:5]([O:22]COC)=[C:6]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[O:16][CH2:15]3)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Cl>CO>[F:26][CH:2]([F:1])[O:3][C:4]1[C:5]([OH:22])=[C:6]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[O:16][CH2:15]3)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67463591HCID 67463591, compound

Product 1

HCID 67466666HCID 67466666, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 5-(3-(difluoromethoxy)-4-methoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one (1 g, 2.7 mmol) in methanol (75 mL) was added concentrated hydrochloride (5 mL) and the reaction mixture was heated to 50° C. for 1 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The obtained residue was basified with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (600 mg, 68%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with dichloromethane (3×)
  4. washThe combined dichloromethane layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e76dc85c505442928ce177ede6b33bb3
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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