Carbon tetrabromide → HCID 14888671, compound

HRID 1647058Notes

Reaction equation

HRID 1647058 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([N:24]1[N:28]=[N:27][C:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36]O)=[CH:32][CH:31]=2)=[N:25]1)([CH3:23])[CH3:22].C(Br)(Br)(Br)[Br:39]>C(OCC)C>[Br:39][CH2:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][C:26]2[N:27]=[N:28][N:24]([C:21]([CH3:23])([CH3:22])[CH3:20])[N:25]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14888703HCID 14888703, compound

Product 1

HCID 14888671HCID 14888671, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triphenylphosphine (6.5 g, 25 mmol) was added to a solution of 4-[[2-(1,1-dimethylethyl)-2H-tetrazol-5yl]-methyl]benzenemethanol (3.0 g, 12.4 mmol) and carbon tetrabromide (8.3 g, 25 mmol) in diethyl ether (150 mL). After 3 hours the reaction mixture was concentrated and the residue purified by chromatography on silica gel eluting with a 9:1 mixture of hexane-ethyl acetate to give 5-[[4-(bromomethyl)phenyl]methyl]-2-(1,1-dimethylethyl)-2H-tetrazole (2.4 g, 7.8 mmol) in 63% yield, mp. 73°-74° C.

Workup

  1. concentrationAfter 3 hours the reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel eluting with a 9:1 mixture of hexane-ethyl acetate

Sources & evidence

ORD record
ord-99b9d7544b65451d851341a55085f124
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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