Carbon tetrabromide → 5-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole

HRID 1621151Notes

Reaction equation

HRID 1621151 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12]O)=[N:10][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>ClCCl>[Br:40][CH2:12][C:11]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 132241301,3-Diphenyl-1H-1,2,4-triazole-5-methanol

Product 1

HCID 866774905-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazoleYield 193.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (1,3-diphenyl-1H-1,2,4-triazol-5-yl)methanol (350 mg, 1.39 mmol) and triphenylphosphine polymer bound (679 mg, 2.02 mmol) in dichloromethane (6 mL) was added at 0-5° C. carbon tetrabromide (670 mg, 2.02 mmol). The ice bath was removed and the mixture was stirred at RT for 18 h. The suspension was filtered, washed with dichloromethane and evaporated to give 844 mg of yellow oil. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless solid (267 mg, 850 μmol, 61.0%).

Workup

  1. customThe ice bath was removed
  2. filtrationThe suspension was filtered
  3. washwashed with dichloromethane
  4. customevaporated

Sources & evidence

ORD record
ord-75e2a941be7c471d9a3bbe7981e190b1
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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