Benzoyl Peroxide → Biphenyl-4-yl-bromo-acetic acid methyl ester

HRID 1512025노트

반응식

HRID 1512025 반응식
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC#N.O>C(Cl)(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[Br:18]

참가 물질

7

반응물 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 30808634-Biphenylylacetic acid methyl esterHCID 18373917Acetonitrile--water (1/1)

생성물 1

HCID 11822880Biphenyl-4-yl-bromo-acetic acid methyl ester수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 5943Carbon Tetrachloride용매

실험 절차

To a stirred solution of biphenyl-4-yl-acetic acid methyl ester (5 g., 22.1 mmol) in carbon tetrachloride (from Acros, 16772) (25 mL) was added N-bromosuccinimide (from Aldrich, 18350) (3.9 g., 22.1 mmol) and benzoyl peroxide (from Acros, 21178) (0.54 g, 2.2 mmol) and the reaction was heated to reflux for 48 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated in vacuo to afford Cpd. 2 as a crude yellow oil (6.24 g., 93% yield). 1HNMR (CDCl3) δH, 3.81, 3H (s, CH3), 5.41, 1H (s, Br—CH), 7.33-7.39, 2H (m, Ar—H), 7.41-7.46, 3H (m, Ar—H), 7.54-7.63, 4H (m, Ar—H); LCMS analysis (solvent MeCN/H2O/0.1% HCO2H, 5-95% gradient/H2O 2.5 min, 95% 4 min., Phenomenex C18 reverse phase, flow rate 1 mL/min.) HPLC retention time 4.39 min.

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto afford Cpd

출처 및 근거

ORD 기록
ord-0fd21d84e9ba4e01826cab4a313f00c7
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217047B2

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