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

HRID 1512025ノート

反応式

HRID 1512025 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0fd21d84e9ba4e01826cab4a313f00c7
出典データセット
uspto-grants-2012_07
特許番号
US08217047B2

反応ノート

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