Benzoic acid, 2-iodo-, methyl ester → Methyl 2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}benzoate

HRID 735340Notes

Reaction equation

HRID 735340 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([O-:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[Na+].I[C:23]1[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([O:27][CH3:28])=[O:26])(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68898972Methyl 2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}benzoateYield 58%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (2.2 g, 7.13 mmol) and methyl 2-iodobenzoate (1.06 mL, 7.0 mmol) according to the methods of Example 6 Step 4. Purification by flash column chromatography eluting with a 20-50% ethyl acetate/isohexane gradient gave methyl 2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}benzoate (1.7 g, 58%). 1H NMR (500 MHz, CDCl3) δ 8.58 (1H, s), 8.25-8.16 (1H, m), 8.06 (1H, d, J=8.5 Hz), 8.01 (1H, s), 8.00-7.92 (2H, m), 7.81 (1H, dd, J=1.7, 8.5 Hz), 7.71-7.54 (5H, m), 7.23-7.13 (2H, m), 3.96 (3H, s); m/z (ES+) 421 [MH+].

Workup

  1. customPurification by flash column chromatography
  2. washeluting with a 20-50% ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-5fe541e0a0b2482385a888c9432021c8
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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