Carbon tetrabromide → 3-(4-bromomethylphenyl)-1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazole

HRID 1038308

Reaction equation

HRID 1038308 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>C1COCC1>[Br:45][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66776992{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol

Product 1

HCID 667770563-(4-bromomethylphenyl)-1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazoleYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of {4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol (P-6; 5.033 g, 15.01 mmol) in THF (100 mL) was added triphenylphosphine (6.009 g, 22.91 mmol). Carbon tetrabromide (7.704 g, 23.23 mmol) dissolved in THF (20 mL) was then added dropwise at room temperature. The mixture was allowed to stir at room temperature for 23 h. It was then filtered through Celite, and the solvent was evaporated at room temperature under vacuum. The crude material was purified by silica gel chromatography, eluting with 50% EtOAc/hexane going to 70% EtOAc/hexane and then 100% EtOAc in a two-step gradient. The title product (4.61 g, 77%) was isolated as a beige solid: mp 124-126° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.25-8.13 (m, 2H), 7.89-7.72 (m, 2H), 7.60-7.47 (m, 2H), 7.47-7.34 (m, 2H), 4.57 (s, 2H); ESIMS m/z 400 (M+2H), 399 (M+H).

Workup

  1. additionwas then added dropwise at room temperature
  2. filtrationIt was then filtered through Celite
  3. customthe solvent was evaporated at room temperature under vacuum
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with 50% EtOAc/hexane going to 70% EtOAc/hexane

Sources & evidence

ORD record
ord-a3bc15047ab049ecbf9d63990fa29676
Source dataset
uspto-grants-2013_10
Patent number
US08551914B2

Linked notes

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