Benzyl Bromide → HCID 57610959, 화합물

HRID 80391

반응식

HRID 80391 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([O:21][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:20])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 806463-(4-Bromobenzoyl)propionic acid

생성물 1

HCID 57610959HCID 57610959, 화합물수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Benzyl bromide (9.98 g, 58.3 mmol) was added to a solution of 4-(4-bromophenyl)-4-oxobutanoic acid (15.0 g, 58.3 mmol) and K2CO3 (3.5 g, 58.3 mmol) in DMF (300 mL) and stirred for 18 hours. The reaction mixture was partitioned between water (200 mL) and ethyl acetate (500 mL). Sat'd NaHCO3 soln (20 mL) was added and the aqueous layer extracted with ethyl acetate (2×) and the combined organic layers were washed with brine and dried and filtered. Concentration gave Example J5, benzyl 4-(4-bromophenyl)-4-oxobutanoate 16 g (79%) which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.35-7.34 (m, 5H), 5.14 (s, 2H), 3.27 (t, J=6.7 Hz, 2H), 2.81 (t, J=6.7 Hz, 2H). HRMS: Anal. C17H16BrNO3 Calcd. 347.0277; found: 347.0283 (M+H)+.

후처리

  1. customThe reaction mixture was partitioned between water (200 mL) and ethyl acetate (500 mL)
  2. additionSat'd NaHCO3 soln (20 mL) was added
  3. extractionthe aqueous layer extracted with ethyl acetate (2×)
  4. washthe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationConcentration

출처 및 근거

ORD 기록
ord-84a5152c782b44fdb0429b093a9b0395
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846023B2

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