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

HRID 1488747Notes

Reaction equation

HRID 1488747 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-pyrazole-3-yl]-4-fluorobenzenemethanol as a white solid: mp 58° C.; 1HNMR (CDCl3) δ2.09 (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-93faaf0c473f47c6bac9162e2c565988
Source dataset
uspto-grants-1997_10
Patent number
US05675017

Reaction notes

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