Sodium Chloride → HCID 21716203, compound

HRID 1385863Notes

Reaction equation

HRID 1385863 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]([C:18]2[CH:23]=[C:22]([OH:24])[C:21]([Cl:25])=[CH:20][C:19]=2[F:26])=[N:10][N:11]([CH3:17])[C:12]=1[O:13][CH:14]([F:16])[F:15].Br[CH2:28][C:29]1[O:30][CH:31]=[CH:32][C:33]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35].[Cl-].[Na+]>CC(C)=O>[Cl:25][C:21]1[CH:20]=[C:19]([F:26])[C:18]([C:9]2[C:8]([Cl:7])=[C:12]([O:13][CH:14]([F:15])[F:16])[N:11]([CH3:17])[N:10]=2)=[CH:23][C:22]=1[O:24][CH2:28][C:29]1[O:30][CH:31]=[CH:32][C:33]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 10799620HCID 10799620, compoundHCID 113248802-Chloro-5-[4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenol

Product 1

HCID 21716203HCID 21716203, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.32 g (16.81 mmoles) of potassium carbonate are added to a solution prepared with 5 g (15.28 mmoles) of 4-chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-difluoromethoxy-1-methylpyrazole, 3.92 g (16.81 mmoles) of ethyl 2-bromomethyl-3-furancarboxylate and 100 ml of acetone. The mixture is heated to reflux temperature under stirring for 2 hours. The raw product is then poured into 500 ml of a saturated solution of sodium chloride and extracted with ethyl acetate (3×150). The joined organic phases are washed with a saturated solution of sodium chloride, anhydrified with sodium sulfate and concentrated under vacuum. The raw product is purified by means of silica gel chromatography using a mixture of hexane/ethyl acetate: 8/2 as eluant. 7.18 g of ethyl 2-[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxymethyl]-3-furancarboxylate (Compound Nr. 2) are obtained (yield 98%), as a white solid having a melting point of 59-61° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. extractionextracted with ethyl acetate (3×150)
  4. washThe joined organic phases are washed with a saturated solution of sodium chloride
  5. concentrationconcentrated under vacuum
  6. customThe raw product is purified by means of silica gel chromatography
  7. additiona mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-9c4d06795cb84a8ea67d633319f68ce7
Source dataset
uspto-grants-2001_07
Patent number
US06265351B1

Reaction notes

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