(2-Bromothiophen-3-yl)methanol → (2-{[6-(4-Fluorophenyl)naphthalen-2-yl]sulfonyl}-3-thienyl)methanol

HRID 735357Notes

Reaction equation

HRID 735357 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([S:26]([O-:28])=[O:27])[CH:20]=[CH:19]3)=[CH:12][CH:11]=1.[Na+]>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([S:26]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[CH2:7][OH:8])(=[O:28])=[O:27])[CH:20]=[CH:19]3)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 12479010(2-Bromothiophen-3-yl)methanolHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68900821(2-{[6-(4-Fluorophenyl)naphthalen-2-yl]sulfonyl}-3-thienyl)methanol

Procedure

Prepared according to the method of Example 6 Step 4 using (2-bromo-3-thienyl)methanol (itself prepared according to WO2004/065384A1) and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate. 1H NMR (400 MHz, d6-DMSO): δ 8.72 (1H, s), 8.36 (2H, d, J=7.9 Hz), 8.21 (1H, d, J=8.8 Hz), 8.04 (2H, dd, J=3.2, 8.4 Hz), 7.93-7.87 (3H, m), 7.38 (2H, t, J=8.9 Hz), 7.26 (1H, d, J=5.1 Hz), 5.47 (1H, t, J=5.9 Hz), 4.70 (2H, d, J=5.9 Hz). m/z (ES+) 384 [(M-OH)+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-766f25f6bd5e4217bed1cc1e21e1e0fb
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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