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

HRID 644681

반응식

HRID 644681 반응식
[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

참가 물질

5

반응물 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 147958715-Bromoisoindoline

생성물 1

HCID 592631135-Bromo-2-trityl-isoindoline수율 85.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7fac7ddaea0a4dcfaacc297eb0d44af4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700625B2

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