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Hydrochloric Acid → HCID 66602549, compound

HRID 2097472
Notes
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Reaction equation

HRID 2097472 reaction equation
CO.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:13])[F:12])=[C:6]([O:14]CC2CC2)[CH:5]=1.Cl>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:12])[F:13])=[C:6]([OH:14])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 100172571-Bromo-3-cyclopropylmethoxy-4-difluoromethoxybenzene

Product 1

HCID 66602549HCID 66602549, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 ml of methanol solution containing 5.80 g (19.7 mmol) of 4-bromo-2-cyclopropylmethoxy-1-difluoromethoxybenzene (see WO 2004033430) was added 60 ml of conc. hydrochloric acid, and the mixture was refluxed for 5 hours. After completion of the reaction, 60 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 4.80 g of the title compound as a slightly yellowish oil substantially quantitatively.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with diethyl ether
  4. customThe organic layer after separation
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-60e6af96f44645dbb01690a0ce83e122
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450319B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes