Trityl chloride → 3-Bromo-2-[2-(1-trityltetrazol-5-yl)-phenyl]-5-methylbenzofuran

HRID 53829Notes

Reaction equation

HRID 53829 reaction equation
C(N(CC)CC)C.[C:8]1([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)Cl)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:28][C:29]1[C:33]2[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=2[O:31][C:30]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[NH:49][N:48]=[N:47][N:46]=1>C(Cl)Cl>[Br:28][C:29]1[C:33]2[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=2[O:31][C:30]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[N:49]([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:48]=[N:47][N:46]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418484HCID 178418484, compound

Product 1

HCID 218480533-Bromo-2-[2-(1-trityltetrazol-5-yl)-phenyl]-5-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.89 g of triethylamine, 8.14 g of triphenylchloromethane and 0.10 g of 4-N,N-dimethylaminopyridine are added in succession to a suspension of 10.37 g of 3-bromo-2-[2'-(1H-tetrazol-5-yl)-phenyl]-5-methylbenzofuran in 300 ml of CH2Cl2 and the batch is stirred for 3 hours at room temperature. The reaction solution is washed with 150 ml of water and 150 ml of brine, concentrated in vacuo to a volume of 50 ml and chromatographed on silica gel 60 (40-63 μm) using CH2Cl2 as eluant. The product, of Rf =0.82 (CH2Cl2 /CH3OH (95:5)), yields crystalline 3-bromo-2-[2'-(1-trityltetrazol-5-yl)-phenyl]-5-methylbenzofuran, m.p. 199°-200°, from ether.

Workup

  1. washThe reaction solution is washed with 150 ml of water and 150 ml of brine
  2. concentrationconcentrated in vacuo to a volume of 50 ml
  3. customchromatographed on silica gel 60 (40-63 μm)

Sources & evidence

ORD record
ord-55aa6cb3da5d4c4d89101c89ca18ac2a
Source dataset
uspto-grants-1997_04
Patent number
US05620998

Reaction notes

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