Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 415172

反応式

HRID 415172 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

生成物 1

HCID 256687Methyl 4-(bromomethyl)benzoate収率 98.8%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

Methyl 4-methylbenzoate 3 (2.9 g, 19.3 mmol) was dissolved in tetrachloromethane (CCl4, 20 mL) at room temperature. N-bromosuccinimide (NBS, 3.5 g, 19.0 mmol) and benzoyl peroxide (BPO, 0.26 g, 1.9 mmol) was added. The resulting mixture was stirred at reflux for 5 hr, then cooled to room temperature, washed with saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1) to get a white solid of methyl 4-(bromomethyl)benzoate (4.3 g, 97%), LC-MS (ESI) m/z 230 [M+1]+.

後処理

  1. temperatureat reflux for 5 hr
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried with anhydrous sodium sulfate and condensed under vacuum
  4. customThe residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1)

出典と根拠

ORDレコード
ord-9a473a965e5e4d0b97aca180d7b8ba63
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

関連ノート

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