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Benzoyl Peroxide → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 230234
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HRID 230234 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH3:11].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:38]
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참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 316201Methyl 5-bromo-2-methylbenzoate

생성물 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
100 °C

실험 절차

5-Bromo-2-methyl-benzoic acid methyl ester (1.31 g, 5.72 mmol) was dissolved in carbon tetrachloride (40 mL). Benzoyl peroxide (10-20 mg) and NBS (1.01 g, 5.72 mmol) were added and the reaction mixture was heated to reflux at 100° C. The reaction course was followed by HPLC and determined to be complete after 1.25 hours. Silica gel was added and the solvent was removed under reduced pressure. The material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent and was determined to be 85% pure by NMR (contained 10% starting material and 5% 5-bromo-2,2-dibromomethyl-benzoic acid methyl ester) and then used without further purification. 1H NMR (300.132 MHz, CDCl3) δ 8.10 (d, J=2.2 Hz, 1H), 7.62 (dd, J=8.3, 2.1 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 4.90 (s, 2H), 4.90 (s, 3H).

후처리

  1. temperaturethe reaction mixture was heated
  2. additionSilica gel was added
  3. customthe solvent was removed under reduced pressure
  4. customThe material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent
  5. customused without further purification

출처 및 근거

ORD 기록
ord-d587078cc49647c0b401dcc940a3b844
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07566727B2

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