Butyl Acrylate → HCID 66733998、化合物

HRID 1929615ノート

反応式

HRID 1929615 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 66733998HCID 66733998、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-482cf023f68c476b9ff7401d21f78deb
出典データセット
uspto-grants-2012_05
特許番号
US08188082B2

反応ノート

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