Water → HCID 59193255, compound

HRID 1259015Notes

Reaction equation

HRID 1259015 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[CH:3][CH:2]=1.[CH:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([F:22])=[CH:19][C:20]=2[F:21])=[CH:13][C:12]([C:23]([OH:25])=[O:24])=[C:11]([OH:26])[CH:10]=1.O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[F:21][C:20]1[CH:19]=[C:18]([F:22])[CH:17]=[CH:16][C:15]=1[C:14]1[CH:9]=[CH:10][C:11]([OH:26])=[C:12]([C:23]([O:25][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:24])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3059DiflunisalHCID 7498Benzyl Bromide

Product 1

HCID 59193255HCID 59193255, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

BnBr (1.35 mL, 11.286 mmol) was added to a solution of diflunisal (2.0 g, 7.99 mmol) in TBAF (10 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (18 h). The organic layer was poured into H2O (15 mL) and extracted with EtOAc (40 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (hexanes) to furnish 2.09 g of benzyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate (white solid, yield: 77%).

Workup

  1. extractionextracted with EtOAc (40 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (hexanes)

Sources & evidence

ORD record
ord-6a2a9bf158574adabe7fc6255d1eb2dd
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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