Borane → 2-chloro-4-fluoro-5-[4-(hydroxymethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

HRID 1488749Notes

Reaction equation

HRID 1488749 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([CH:20]=[O:21])=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[N:16]=2)=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].B>O1CCCC1>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([CH2:20][OH:21])=[C:18]([C:22]([F:23])([F:24])[F:25])[N:17]([CH3:26])[N:16]=2)=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 572606202-Chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

Product 1

HCID 571742762-chloro-4-fluoro-5-[4-(hydroxymethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.5 g of 2-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester in 50ml of anhydrous tetrahydrofuran was added 4 mL of 1M borane in THF solution. The reaction was stirred overnight and then poured onto water, extracted into diethyl ether, dried over anhydrous magnesium sulfate and concd in vacuo to give 0.5 g of 2-chloro-4-fluoro-5-[4-(hydroxymethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester as a clear oil: 1HNMR CDCl3) δ8.10 (d, 1H J=7.7,), 7.36 (d, 1H, J=9.6), 5.29 (m, 1H), 4.62 (s, 2H), 4.10 (s, 3H), 1.42 (d, 6H, J=6.6); 19FNMR CDCl3) ppm: -58.82, -109.09.

Workup

  1. additionpoured onto water
  2. extractionextracted into diethyl ether
  3. dry with materialdried over anhydrous magnesium sulfate and concd in vacuo

Sources & evidence

ORD record
ord-87f0b244281d46429a5a3af476c7f095
Source dataset
uspto-grants-1997_10
Patent number
US05675017

Reaction notes

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