1-Fluoro-2-iodobenzene → 2-(4-Fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthalene

HRID 735371Notes

Reaction equation

HRID 735371 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+].[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1I>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:18]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[F:22])(=[O:20])=[O:19])[CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 676731-Fluoro-2-iodobenzeneHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 689024302-(4-Fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthaleneYield 30%

Procedure

The title compound was prepared from sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (2.2 g, 7.13 mmol) and 1-fluoro-2-iodobenzene (820 μL, 7.03 mmol) according to the method of Example 6 Step 4. Purification by flash column chromatography eluting with 60% dichloromethane/isohexane gave 2-(4-fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthalene (0.80 g, 30%). 1H NMR (500 MHz, CDCl3) δ 8.66 (1H, s), 8.20-8.18 (1H, m), 8.07 (1H, d, J=8.5 Hz), 8.03 (1H, s), 7.98 (1H, d, J=8.7 Hz), 7.94 (1H, d, J=8.7 Hz), 7.83 (1H, dd, J=1.7, 8.5 Hz), 7.71-7.62 (2H, m), 7.60-7.56 (1H, m), 7.38-7.30 (1H, m), 7.21-7.17 (2H, m), 7.14-7.05 (1H, m).

Workup

  1. customPurification by flash column chromatography
  2. washeluting with 60% dichloromethane/isohexane

Sources & evidence

ORD record
ord-69c8883e3a8a468d8e9eb27394bd6647
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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