Benzoyl Peroxide → (6-(Bromomethyl)-2-methoxybenzyl)phthalimide

HRID 1157848ノート

反応式

HRID 1157848 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:4]=1[CH2:5][C:6]1[CH:16]=[CH:15][CH:14]=[C:8]2[C:9]([NH:11][C:12](=[O:13])[C:7]=12)=[O:10].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[Br:22][CH2:21][C:17]1[C:4]([CH2:5][C:6]2[CH:16]=[CH:15][CH:14]=[C:8]3[C:9]([NH:11][C:12](=[O:13])[C:7]=23)=[O:10])=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21985073(2-Methoxy-6-methylbenzyl)phthalimide

生成物 1

HCID 21985106(6-(Bromomethyl)-2-methoxybenzyl)phthalimide収率 86.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of (2-methoxy-6-methylbenzyl)phthalimide (0.286 g, 1.02 mmol) in CCl4 (25 mL) was added recrystallized N-bromosuccinimide (0.177 g, 0.99 mmol) followed by benzoyl peroxide (28 mg, 0.11 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (25 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (3:1 hexanes-EtOAc) provided 0.31 g (86%) of (6-(bromomethyl)-2-methoxybenzyl)phthalimide as a white solid. 1H NMR (CDCl3) δ 3.78 (s, 3H), 4.90 (s, 2H), 5.00 (s, 2H), 6.83 (d, 1H, J=8.4 Hz), 6.98 (d, 1H, J=7.2 Hz), 7.25 (dd, 1H, J=7.2, 8.4 Hz), 7.67-7.69 (m, 2H), 7.78-7.81 (m, 2H). ES-MS m/z 382 (M+Na), 384 (M+Na).

後処理

  1. temperatureto reflux for 90 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (3:1 hexanes-EtOAc)

出典と根拠

ORDレコード
ord-119c3bfc9175488088c1bfc2366b407a
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

反応ノート

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