m-Chloroperbenzoic acid → 4-[2-(Benzyloxy)-4-ethylphenoxy]-3-fluorophenyl acetate

HRID 626060Notes

Reaction equation

HRID 626060 reaction equation
[CH2:1]([O:8][C:9]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[CH:22][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15](C(=O)C)=[CH:14][C:13]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=[C:30]([C:35]([O:37]O)=[O:36])C=1>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1>[C:35]([O:37][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]2[CH:22]=[CH:23][C:24]([CH2:26][CH3:27])=[CH:25][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:13]([F:21])[CH:14]=1)(=[O:36])[CH3:30]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 591914011-{4-[2-(Benzyloxy)-4-ethylphenoxy]-3-fluorophenyl}ethanone

Product 1

HCID 591913664-[2-(Benzyloxy)-4-ethylphenoxy]-3-fluorophenyl acetateYield 51%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{4-[2-(benzyloxy)-4-ethylphenoxy]-3-fluorophenyl}ethanone (3 g, 8.24 mmol) in dry dichloromethane (30 ml), was added PTSA (0.047 g, 0.247 mmol). The reaction mixture was cooled in an ice bath and mCPBA (50% H2O)(2.84 g, 8.24 mmol) was added portionwise. The resulting mixture was stirred at RT for 3 days, then concentrated at 35-40 C. The residue was purified by column chromatography, (pet ether:EtOAC). The resulting solid was dissolved in pet ether, filtered then concentrated the yield the title compound (1.6 g; 51%)

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. concentrationconcentrated at 35-40 C
  3. customThe residue was purified by column chromatography, (pet ether:EtOAC)
  4. dissolutionThe resulting solid was dissolved in pet ether
  5. filtrationfiltered
  6. concentrationthen concentrated the

Sources & evidence

ORD record
ord-57d4d877fb35412883c0fbcee38cda50
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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