m-Chloroperbenzoic acid → (1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanol

HRID 735315Notes

Reaction equation

HRID 735315 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@@H:30]([OH:32])[CH3:31])[CH:17]=[CH:16]2.[OH-:33].[Ca+2].[OH-:35]>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@@H:30]([OH:32])[CH3:31])(=[O:35])=[O:33])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 68901000(1S)-1-{2-[(6-bromo-2-naphthyl)thio]phenyl}ethanol

Product 1

HCID 68899466(1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanolYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (2.85 g, 12.7 mmol) was added to a stirred solution of (1S)-1-{2-[(6-bromo-2-naphthyl)thio]phenyl}ethanol (2.28 g, 6.3 mmol) in dichloromethane (50 mL) at ambient temperature under nitrogen. Calcium hydroxide (1.50 g, 20.2 mmol) was added after 2 hours, stirred for a further 1 hour then filtered and concentrated in vacuo. Purification by flash column chromatography eluting with a 10-40% ethyl acetate/isohexane gradient followed by trituration using isohexane gave solid (1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanol (1.47 g, 59%). 1H NMR (500 MHz, CDCl3) δ 8.50 (1H, s), 8.16 (1H, d, J 7.9 Hz), 8.08 (1H, s), 7.90-7.82 (2H, m), 7.77-7.70 (3H, m), 7.67 (1H, t, J 7.5 Hz), 7.50 (1H, t, J 7.7 Hz), 5.60 (1H, q, J 6.3 Hz), 2.46 (1H, s), 1.33 (3H, d, J 6.3 Hz); m/z (ES+) 373, 375 [(M-OH)+].

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash column chromatography
  4. washeluting with a 10-40% ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-db4dbeb7049d429e80825e595edde200
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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