Triethylamine → HCID 21075354, 화합물

HRID 1396663노트

반응식

HRID 1396663 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

반응 조건

온도
70 °C

실험 절차

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

출처 및 근거

ORD 기록
ord-f7a70c10310f4255be7ead246593d315
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901126B2

반응 노트

불러오는 중…