Butyl Acrylate → HCID 66733998, 화합물

HRID 1929615노트

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HRID 1929615 반응식
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1.[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[CH2:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1)[CH2:17][CH2:18][CH3:19]

참가 물질

8

반응물 4

HCID 8846Butyl AcrylateHCID 9237DabcoHCID 11430Potassium CarbonateHCID 27832155-bromo-1,3-difluoro-2-methylbenzene

생성물 1

HCID 66733998HCID 66733998, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To a solution of 5-bromo-1,3-difluoro-2-methyl-benzene (6.910 g; 33.379 mmol) in anhydrous DMF (200 ml) were added successively butyl acrylate (7.15 ml; 50.062 mmol), DABCO (157 mg; 1.333 mmol), potassium carbonate (4.612 g; 33.379 mmol), and palladium acetate (150 mg; 0.669 mmol). The resulting brown suspension was heated to 120° C. for 1 h. The reaction mixture was allowed to cool to rt before ether (400 ml) was added. This mixture was then washed with water (2×200 ml), and the mixed aq. layers were further extracted with ether (150 ml). The combined organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/heptane=1/1=>DCM) gave the pure product 3-(3,5-difluoro-4-methyl-phenyl)-acrylic acid butyl ester as a yellow oil which was further dried under HV (4.690 g; 55%). LC-MS: tR=1.10 min.; [M+H]+: no ionisation.

후처리

  1. additionwas added
  2. washThis mixture was then washed with water (2×200 ml)
  3. extractionthe mixed aq. layers were further extracted with ether (150 ml)
  4. dry with materialThe combined organic layers were dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/heptane=1/1=>DCM)

출처 및 근거

ORD 기록
ord-482cf023f68c476b9ff7401d21f78deb
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188082B2

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