m-Chloroperbenzoic acid → HCID 69931103, compound

HRID 1977927Notes

Reaction equation

HRID 1977927 reaction equation
[CH2:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[C:19]([OH:21])[C:18]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:17][C:16]=2[CH2:29][CH3:30])=[CH:8][CH:7]=[CH:6][C:5]=1[S:31]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=[O:36])=[O:32])[CH2:2][CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:47]>C(Cl)Cl>[OH2:10].[CH2:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[C:19]([OH:21])[C:18]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:17][C:16]=2[CH2:29][CH3:30])=[CH:8][CH:7]=[CH:6][C:5]=1[S:31]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=[O:36])(=[O:47])=[O:32])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10793277HCID 10793277, compound

Product 1

HCID 69931103HCID 69931103, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

To a solution of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenylsulfinyl]benzoic acid (150 mg, 0.260 mmol) in methylene chloride (3.0 mL) at 0° C. was added a solution of 85% m-chloroperoxybenzoic acid (53 mg) in methylene chloride (1 mL). After 1 hour the mixture was warmed to 4° C. and stirred for 18 hours. The mixture was concentrated in vacuo; purification of the residue via silica gel chromatography (90% chloroform/9.5% methanol/0.5% acetic acid) provided 90 mg (58%) of the title product as a white solid: mp 80-90° C.; NMR (DMSO-d6) 7.88 (m, 2H), 7.55-7.78 (m, 3H), 7.50 (m, 2H), 7.33 (m, 2H), 7.04 (m, 2H), 6.95 (s, 1H), 6.51 (s, 1H), 4.19 (t, J=4.8 Hz, 2H), 4.05 (t, J=5.8 Hz, 2H), 2.69 (m, 2H), 2.44 (q, J=5.8 Hz, 2H), 2.19 (m, 2H), 0.90-1.10 (m, 5H), 0.71 (t, J=4.5 Hz, 3H); MS-FD m/e 595 (p+2, 30), 594 (p+1, 40), 593 (p, 100); IR (CHCl3, cm−1) 2966, 1730, 1603, 1497, 1299, 1146.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurification of the residue via silica gel chromatography (90% chloroform/9.5% methanol/0.5% acetic acid)

Sources & evidence

ORD record
ord-2648b54d8c18478e98e8e70cd26a9508
Source dataset
uspto-grants-2001_05
Patent number
US06235785B1

Reaction notes

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