Triethylamine → HCID 21075354, 화합물

HRID 1807856노트

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HRID 1807856 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][O:10][CH3:11].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=O.[C:50]([O:53][CH2:54]C)(=[O:52])C>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:50]([O:53][CH3:54])=[O:52])=[C:3]([CH2:9][O:10][CH3:11])[CH:4]=1

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 27694141-bromo-4-fluoro-2-(methoxymethyl)benzeneHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 21075354HCID 21075354, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매HCID 962Water용매

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온도
70 °C

실험 절차

Under an argon atmosphere, to a solution of 3.45 g of 1-bromo-4-fluoro-2-(methoxymethyl)benzene in 20 mL of dimethylsulfoxide were added 353 mg of palladium acetate, 650 mg of 1,3-bis(diphenylphosphino)propane, 4.4 mL of triethylamine, and 10 mL of methanol in this order, and the atmosphere in the reaction container were replaced with carbon monoxide, followed by stirring at 70° C. for 6 hours. The reaction mixture was poured into a mixed liquid of water and ethyl acetate. The aqueous layer was separated, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 1.75 g of methyl 4-fluoro-2-(methoxymethyl)benzoate.

후처리

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-f50bdf6dd6264dd09309f3bab55a16d0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357688B2

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