Benzyl Bromide → HCID 68753687, 화합물

HRID 333322

반응식

HRID 333322 반응식
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>CN(C=O)C.O>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:30][C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[O:10])=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 7498Benzyl Bromide2회HCID 11430Potassium CarbonateHCID 30824342(4-Biphenyl)propionic acid

생성물 1

HCID 68753687HCID 68753687, 화합물수율 88.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 3-(biphenyl-4-yl)propanoic acid (5 g, 22.10 mmol) and K2CO3 (6.11 g, 44.2 mmol) in DMF (22 ml), BnBr (3.94 ml, 33.1 mmol) was added. After stirred for 15 hours, additional BnBr (3.94 ml, 33.1 mmol) was added. After stirred for further 22 hours, the reaction was diluted with H2O, extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was diluted with EtOAc (150 ml), and NH-silica gel was added to the suspension. The EtOAc was evaporated, and the resulted slurry was allowed to stir for 1 hour. The slurry was eluted with 10% EtOAc/heptane (150 ml) to give benzyl 3-(biphenyl-4-yl)propanoate (6.16 g); Retention time=1.71 minutes (condition A); 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (t, J=7.8 Hz, 2H) 3.01 (t, J=7.8 Hz, 2H) 5.12 (s, 2H) 7.21-7.47 (m, 14H).

후처리

  1. additionwas added
  2. stirringAfter stirred for further 22 hours
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe obtained residue was diluted with EtOAc (150 ml), and NH-silica gel
  9. additionwas added to the suspension
  10. customThe EtOAc was evaporated
  11. stirringto stir for 1 hour
  12. washThe slurry was eluted with 10% EtOAc/heptane (150 ml)

출처 및 근거

ORD 기록
ord-b78513581fb14ee78dd3ce13c4628a39
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

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