Ethanol → HCID 86748307, compound

HRID 1492080Notes

Reaction equation

HRID 1492080 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1(C(O)=O)[CH2:11][CH2:10]1.[OH-:15].[K+].[K].[CH3:18][O:19][N:20]=[C:21]([C:26]1[CH:31]=[CH:30][CH:29]=CC=1CBr)[C:22]([O:24][CH3:25])=[O:23].C(O[CH:38]([CH3:40])[CH3:39])(C)C.[CH2:41]([OH:43])C>CN1CCCC1=O>[CH3:18][O:19][N:20]=[C:21]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:10][C:11]=1[CH:9]([O:15][C:41]([CH:38]1[CH2:40][CH2:39]1)=[O:43])[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[C:22]([O:24][CH3:25])=[O:23]

Participants

8

Reactant 6

HCID 702EthanolHCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 149962881-(2,6-difluorophenyl)cyclopropanecarboxylic acid2×HCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 86748307HCID 86748307, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A method similar to Example 2 was used and 11.8 g (60 mmol) of 1-(2,6-difluorophenyl )-cyclopropanecarboxylic acid, prepared according to Example 8b and dissolved in 60 ml of ethanol, were converted with 3.6 g (64 mmol) of potassium hydroxide to the potassium salt of 2,6-difluorophenylcyclopropanecarboxylic acid, and said salt was then reacted, at 90° C., in 100 ml of N-methylpyrrolidone, with 13.3 g (47 mmol) of 2-(bromomethyl)phenylglyoxylic acid methyl ester O-methyloxime. The resulting oily product was covered with a layer of diisopropyl ether and was crystallized by rubbing the wall of the vessel. Yield: 85%; mp.: 122°-123° C.; white crystals.

Workup

  1. customwas crystallized

Sources & evidence

ORD record
ord-2d5b6bac8f284af48d1c8d8218e2286d
Source dataset
uspto-grants-1994_12
Patent number
US05371268

Reaction notes

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