Ethyl 3,4-Dihydroxybenzoate → 2,2-Bis-(3,5-difluoro-phenyl)-benzo[1,3]dioxole-5-carboxylic acid ethyl ester

HRID 2103145Notes

Reaction equation

HRID 2103145 reaction equation
Cl[C:2](Cl)([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)[C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=1.[OH:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][C:31]=1[OH:32])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>ClCCl>[CH2:27]([O:26][C:24]([C:23]1[CH:29]=[CH:30][C:31]2[O:32][C:2]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=3)([C:3]3[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=3)[O:20][C:21]=2[CH:22]=1)=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 77547Ethyl 3,4-DihydroxybenzoateHCID 22475077HCID 22475077, compound

Product 1

HCID 690590952,2-Bis-(3,5-difluoro-phenyl)-benzo[1,3]dioxole-5-carboxylic acid ethyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

239 mg dichloro-bis(3,5-difluorophenyl)methane and 141 mg ethyl 3,4-dihydroxybenzoate were heated to 180° C. for 2 h 15 min. The brown mixture was diluted with dichloromethane, washed with sat. NaHCO3 solution and water. The dried solution was evaporated and the residue purified on silica gel to provide 284 mg resinous oil. MS: 419 ([M+H]+).

Workup

  1. washwashed with sat. NaHCO3 solution and water
  2. customThe dried solution was evaporated
  3. customthe residue purified on silica gel

Sources & evidence

ORD record
ord-f087e36070194054b21cb37685a6aea7
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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