Carbon tetrabromide → 4-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1862472Notes

Reaction equation

HRID 1862472 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11]O)=[C:9]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[N:8]([CH:22]([CH3:24])[CH3:23])[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][Br:45])=[C:9]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[N:8]([CH:22]([CH3:24])[CH3:23])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 693543045-(3,5-dichlorophenylthio)-4-hydroxymethyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 693555624-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl esterYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 504 mg 5-(3,5-dichlorophenylthio)-4-hydroxymethyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester in 5 ml of dichloromethane was added 375 mg of triphenylphosphine and 474 mg of carbon tetrabromide. The reaction mixture was stirred overnight. The solvent was removed and the residue was purified by flash chromatography on silica gel using diethyl ether/iso-hexane for the elution to give 367 mg of 4-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester as a colourless gum. Mass spectrum (ES) m/z 451 [M+H]+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-b3b433b13407481f94a27ec444dd1119
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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