Triethylamine → ethyl 3-chloro-2-hydroxy-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzoate

HRID 629363Notes

Reaction equation

HRID 629363 reaction equation
[Cl:1][C:2]1[C:3]([OH:27])=[C:4]([CH:8]=[C:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[C:28](Cl)(=O)[C:29](Cl)=O.C(N(CC)CC)C>ClCCl.C(O)C>[Cl:1][C:2]1[C:3]([OH:27])=[C:4]([CH:8]=[C:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:20][CH:21]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([O:7][CH2:28][CH3:29])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1184684273-chloro-2-hydroxy-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzoic acid

Product 1

HCID 118468416ethyl 3-chloro-2-hydroxy-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzoateYield 31.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 3-chloro-2-hydroxy-5-[4-(1H-pyrazol-1-yl)benzyl]-4-(trifluoromethyl)benzoic acid (0.60 g) in dichloromethane (20.0 mL) was added oxalyl chloride (0.29 g) under ice-cooling, and the mixture was stirred at 15° C. for 16 hr. The reaction mixture was added to a solution of triethylamine (2.00 mL) in ethanol (40.0 mL), and the mixture was stirred for 1 hr. The mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with 1N hydrochloric acid and saturated aqueous sodium bicarbonate solution, and the organic layer was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (0.20 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe mixture was washed with 1N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-afbb3f40ac564f179956f28177bb4c02
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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