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

HRID 424125

Reaktionsgleichung

Reaktionsgleichung von HRID 424125
[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

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 147958715-Bromoisoindoline

Produkt 1

HCID 592631135-Bromo-2-trityl-isoindolineAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3c6a029389d0433c8524802a8a01be98
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101648B2

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