Trityl chloride → 5-Bromo-2-trityl-isoindoline

HRID 644681

反応式

HRID 644681 の反応式
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25]2.C(N(CC)CC)C>ClCCl>[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26]([C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:25]2

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 147958715-Bromoisoindoline

生成物 1

HCID 592631135-Bromo-2-trityl-isoindoline収率 85.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trityl chloride (2.30 g, 8.23 mmol) was added to a solution of 5-bromo-2,3-dihydro-1H-isoindole (1.64 g, 8.23 mmol) and triethylamine (1.4 mL, 9.9 mmol) in dichloromethane (20 mL). After 18 hours the solvent was removed in vacuo, the residue taken up in ethyl acetate and washed with water (×2) and brine, dried (MgSO4) and concentrated. The crude material was purified by flash chromatography on silica eluting with 1% triethylamine/10% ethyl acetate/petrol to give 5-bromo-2-trityl-2,3-dihydro-1H-isoindole as a reddish-brown solid (3.10 g, 85%). 1H NMR (CDCl3) 7.91-7.84 (1H, m), 7.57 (6H, d), 7.45-7.41 (1H, m), 7.33-7.14 (9H, m), 6.95 (1H, d), 3.90 (2H, s), 3.86 (2H, s). MS: Ph3C+ 243.

後処理

  1. customAfter 18 hours the solvent was removed in vacuo
  2. washwashed with water (×2) and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography on silica eluting with 1% triethylamine/10% ethyl acetate/petrol

出典と根拠

ORDレコード
ord-7fac7ddaea0a4dcfaacc297eb0d44af4
出典データセット
uspto-grants-2010_04
特許番号
US07700625B2

関連ノート

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