m-Chloroperbenzoic acid → 4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol formate

HRID 2225795Notes

Reaction equation

HRID 2225795 reaction equation
ClC1C=CC=C([C:8]([O:10]O)=[O:9])C=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20](C=O)=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1>ClCCl>[CH:8]([O:10][C:20]1[C:19]([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=2)=[CH:24][CH:23]=[CH:22][C:21]=1[CH:25]([CH3:26])[CH3:27])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 190044654'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-carboxaldehyde

Product 1

HCID 190043884'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol formateYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (4.73 g) was added to a solution of 4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-carboxaldehyde (3.55 g) in dichloromethane (100 mL) and the reaction mixture was stirred at room temperature overnight. The precipitated solids were removed by filtration and the filtrate was washed in turn with water, saturated sodium bisulfite solution, sodium bicarbonate solution and brine. After the dried (MgSO4) organic layer was evaporated, the crude product was purified by HPLC (ethyl acetate-hexane; 1:49) to afford 2.5 g of 4'-fluoro-3-(1-methylethyl)[1,1'biphenyl]-2-ol formate as a oil.

Workup

  1. customThe precipitated solids were removed by filtration
  2. washthe filtrate was washed in turn with water, saturated sodium bisulfite solution, sodium bicarbonate solution and brine
  3. dry with materialAfter the dried (MgSO4) organic layer
  4. customwas evaporated
  5. customthe crude product was purified by HPLC (ethyl acetate-hexane; 1:49)

Sources & evidence

ORD record
ord-4f5c1c27fdd84077a1a5a2d9f8e4387f
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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