Hydrochloric Acid → HCID 66602702, compound

HRID 2097481Notes

Reaction equation

HRID 2097481 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[C:4]([O:12][CH:13]([CH:16]2[CH2:18][CH2:17]2)[C:14]#[CH:15])[CH:3]=1.C(N(CC)C1C=CC=CC=1)C.Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[C:4]2[C:3]=1[CH:15]=[CH:14][CH:13]([CH:16]1[CH2:18][CH2:17]1)[O:12]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 86627035HCID 86627035, compound

Product 1

HCID 66602702HCID 66602702, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To 545 mg (1.7 mmol) of 4-bromo-2-(1-cyclopropyl-2-propynyloxy)-1-difluoromethoxybenzene obtained in Reference example 14-(b) was added 5 ml of N,N-diethylaniline, and the mixture was stirred at 200° C. for 2 hours. After completion of the reaction, water was added to the reaction mixture, and then, a pH of the mixture was adjusted to 1 with conc. hydrochloric acid, 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=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 339 mg of the title compound as yellowish liquid. (Yield: 63%)

Workup

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

Sources & evidence

ORD record
ord-3b5858ecef7b445da3f1a5ff7e091e44
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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