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Carbon tetrabromide → 2-(6-bromoheptyl)-1H-benzimidazole

HRID 2414789
Notes
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Reaction equation

HRID 2414789 reaction equation
O[CH:2]([CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:19][CH:2]([CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 226434112-(6-hydroxyheptyl)-1H-benzimidazole

Product 1

HCID 226434292-(6-bromoheptyl)-1H-benzimidazoleYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.18 g of the compound obtained in Example 19a, 4.97g of carbon tetrabromide and 3.93 g of triphenylphosphine were added to 30 ml of tetrahydrofuran and the mixture was reacted overnight at room temperature. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 2.10 g of the title compound as pale yellow solid (yield: 75%).

Workup

  1. customthe mixture was reacted overnight at room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-caf644fbcd154e109d938944ddf8b008
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06815455B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes