Borane;tetrahydrofuran → 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanol

HRID 1379816Notes

Reaction equation

HRID 1379816 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([CH3:17])=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([CH3:17])=[C:15]([C:18]([F:19])([F:21])[F:20])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 229064292-Chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid

Product 1

HCID 229064162-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanolYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5 g of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid (Ex. 2) in 30 mL of anhydrous THF was treated with 10 mL of 1.0M borane-THF solution and heated to reflux for 24 hr. The mixture was allowed to cool and added to ice water. A precipitate formed which was collected by filtration, washed with cold water and dried to give 1.3 g of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanol as a white solid: mp 58° C.; 1HNMR (CDCl3) δ 2.09 (q, 3H), 4.00 (s, 3H), 4.75 (s, 2H), 7.20 (d, 1H), 7.57 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hr
  3. temperatureto cool
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-4207080b718841048f6059518dbda2b9
Source dataset
uspto-grants-1997_09
Patent number
US05672715

Reaction notes

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