Carbon tetrabromide → 4-bromomethyl-1-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazole

HRID 1192946Notes

Reaction equation

HRID 1192946 reaction equation
[CH3:1][N:2]1[C:6]([O:7][CH:8]2[CH2:11][O:10][CH2:9]2)=[C:5]([CH2:12]O)[C:4]([C:14]([F:17])([F:16])[F:15])=[N:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:12][C:5]1[C:4]([C:14]([F:17])([F:16])[F:15])=[N:3][N:2]([CH3:1])[C:6]=1[O:7][CH:8]1[CH2:11][O:10][CH2:9]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59739609[1-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazol-4-yl]-methanol

Product 1

HCID 597396184-bromomethyl-1-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazoleYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-Methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazol-4-yl]-methanol (8.14 g, 32.3 mmol) was dissolved in dichloromethane (100 ml) and triphenyl phosphine (8.96 g, 34.2 mmol) and carbon tetrabromide (10.31 g, 31.05 mmol) were added. The solution was stirred for 2 hours and concentrated to give an orange oil. Purification by chromatography on silica gel (eluent: ethyl acetate/hexane) yielded the product as an orange oil (10.1 g) which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customto give an orange oil
  3. customPurification by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5c93fee380784330be259ddf42cebaf3
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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