Triethylamine → Ethyl 2-(4-bromo-2,5-difluoro-3-methylbenzoyl)-3-dimethylaminoacrylate

HRID 1917423

반응식

HRID 1917423 반응식
[F:1][C:2]1[C:10]([CH3:11])=[C:9]([Br:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[CH3:18][N:19]([CH3:27])[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[Br:12][C:9]1[C:8]([F:13])=[CH:7][C:3]([C:4]([C:21](=[CH:20][N:19]([CH3:27])[CH3:18])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:6])=[C:2]([F:1])[C:10]=1[CH3:11]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 212202454-Bromo-2,5-difluoro-3-methylbenzoic acid

생성물 1

HCID 86664658Ethyl 2-(4-bromo-2,5-difluoro-3-methylbenzoyl)-3-dimethylaminoacrylate수율 71.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

2,5-Difluoro-4-bromo-3-methylbenzoic acid (10.7 g, 42.4 mmol) was dissolved in toluene (160 mL). Thionyl chloride (5.00 mL, 63.9 mmol) and dimethylformamide (5.0 mL) were added, and the mixture was heated to reflux for two hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (300 mL). Ethyl 3-dimethylaminoacrylate (7.30 ml, 50.9 mmol) and triethylamine (7.60 mL, 54.5 mmol) were added, and the mixture was heated to reflux for three hours. The solvent was evaporated under reduced pressure, and dichloromethane and water were added to the residue to separate the layers. Then, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to flash column chromatography (hexane:ethyl acetate=2:1→1:1→1:2) to give the title compound (11.35 g) as a yellow oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for two hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in tetrahydrofuran (300 mL)
  5. temperaturethe mixture was heated
  6. temperatureto reflux for three hours
  7. customThe solvent was evaporated under reduced pressure, and dichloromethane and water
  8. additionwere added to the residue
  9. customto separate the layers
  10. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-bb4c6055209d45bfa7fdc50545f1e448
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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