Benzoyl Peroxide → Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

HRID 923240ノート

反応式

HRID 923240 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH:4]([Br:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14897830Methyl 2-(3-fluoro-4-methoxyphenyl)acetate

生成物 1

HCID 58827055Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

The (3-fluoro-4-methoxyphenyl)acetic acid methyl ester (5.16 g, 26.0 mmol) is dissolved in carbon tetrachloride (300 mL) along with NBS (5.56 g, 31.3 mmol) and benzoyl peroxide (0.63 g, 2.60 mmol) and refluxed for 2 h. The solution is then allowed to cool to room temperature and is filtered. The filtrate is evaporated and the residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8) to give bromo-(3-fluoro-4-methoxyphenyl)acetic acid methyl ester as a yellow oil. 1H NMR (CDCl3) δ 7.37 (d, J=12 Hz, 1H), 7.26-7.23 (m, 1H), 6.93 (t, J=8 Hz, 1H), 5.31 (s, 1H), 3.91 (s, 3H), 3.81 s, 3H).

後処理

  1. temperaturerefluxed for 2 h
  2. filtrationis filtered
  3. customThe filtrate is evaporated
  4. customthe residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8)

出典と根拠

ORDレコード
ord-337ea27808bf47a2af7b7956e565da1e
出典データセット
uspto-grants-2016_03
特許番号
US09278969B2

反応ノート

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