Water → HCID 67954031, compound

HRID 1259027Notes

Reaction equation

HRID 1259027 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[CH:11]1[C:16]([C:17]2[CH:18]=[CH:19][C:20]([F:24])=[CH:21][C:22]=2[F:23])=[CH:15][C:14]([C:25]([OH:27])=[O:26])=[C:13]([OH:28])[CH:12]=1.O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[F:23][C:22]1[CH:21]=[C:20]([F:24])[CH:19]=[CH:18][C:17]=1[C:16]1[CH:11]=[CH:12][C:13]([OH:28])=[C:14]([C:25]([O:27][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:26])[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3059DiflunisalHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 67954031HCID 67954031, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

PMBBr (1.20 mL, 8.325 mmol) was added to a solution of diflunisal (1.50 g, 5.995 mmol) in TBAF (7 mL, 1 M solution in THF) and the mixture was stirred at r.t. overnight (16 h). The reaction mixture was poured into H2O (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5→10% EtOAc/hexanes) to furnish 1.85 g of 4-methoxybenzyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate (white solid, yield: 83%).

Workup

  1. extractionextracted with EtOAc (70 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (5→10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e080379ab32a4b66ad83aef3fbb6c67c
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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