m-Chloroperbenzoic acid → HCID 10834141, compound

HRID 1598361Notes

Reaction equation

HRID 1598361 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][C:10]2([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=3)=[O:16])[CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Cl[C:27]1C=CC=C(C(OO)=O)C=1.[S:37](=[O:40])(O)[O-:38].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:25])[CH2:9][C:10]2([CH2:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([S:37]([CH3:27])(=[O:40])=[O:38])=[CH:21][CH:22]=3)=[O:16])[CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10522248HCID 10522248, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 10834141HCID 10834141, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 18.3 g (51.4 mmol) of 1-(4-fluorophenyl)-2-[1-[2-[4-(methylthio)phenyl]-2-oxoethyl]cyclobutan-1-yl]ethan-1-one (prepared in Step 5) in 200 mL of chloroform at 10° C. was slowly treated with 35.6 g (ca. 103 mmol) of solid m-chloroperbenzoic acid (50-60%). The reaction was allowed to stir for 30 minutes and treated with aqueous sodium bisulfite. The chloroform was removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate extracts were washed 3 times with saturated sodium bicarbonate and once with brine, dried (MgSO4), and concentrated in vacuo to give 19.27 g (97%) of 1-(4-fluorophenyl)-2-[1-[2-[4-(methylsulfonyl)phenyl]-2-oxoethyl]cyclobutan-1-yl]ethan-1-one as an oil: NMR (CDCl3) δ1.95-2.06 (M, 2H), 2.11 (t, J=7 Hz, 4H), 3.05 (s, 3H), 3.52 (s, 2H), 3.59 (s, 2H), 7.09 (t, J=9 Hz, 2H), 7.92-8.04 (m, 4H), 8.19 (d, J=9 Hz, 2H).

Workup

  1. customThe chloroform was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe ethyl acetate extracts were washed 3 times with saturated sodium bicarbonate
  4. dry with materialonce with brine, dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90785c1bb72641f5832bff06367edb7b
Source dataset
uspto-grants-1998_04
Patent number
US05736579

Reaction notes

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