Iodine → Methanesulfonic acid 4-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester

HRID 1873140Notes

Reaction equation

HRID 1873140 reaction equation
[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4.II.[I:31](O)(=O)=O.S(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C.S(=O)(=O)(O)O>[I:31][C:17]1[C:7]2[S:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:9]=3[C:8]=2[C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2

Participants

8

Reactant 4

HCID 807IodineHCID 24345Iodic acidHCID 15481262Methanesulfonic acid 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl EsterHCID 23665763Sodium Bisulfite

Product 1

HCID 15481264Methanesulfonic acid 4-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl esterYield 373%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methanesulfonic acid 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl ester (2.24 g, 5.54 mmole) in tetrahydrofuran (22.4 mL), 80% aqueous acetic acid (11.2 mL) and sulfuric acid (0.6 mL) was added iodine (0.984 g, 3.87 mmol) and iodic acid (0.244 g, 1.39 mmol). The reaction mixture was stirred for 88 h at room temperature then combined with an aqueous solution of sodium bisulfite (100 mL). The organics were extracted with ether (500 mL). The extracts were concentrated and chased with benzene and pet ether to provide the title compound as a yellow solid (2.75 g, 94%): mp 176-186° C.; NMR (CDCl3); δ 8.24 (ddd, J=8, 1, 1 Hz, 1H), 7.81 (ddd, J=8, 1, 1 Hz, 1H), 7.65-7.58 (m, 3H), 7.52-7.38 (m, 5H), 7.11-7.07 (ddd, J=8, 7, 1 Hz, 1H), 6.57 (ddd, J=8, 1, 1 Hz, 1H), 3.33 (s, 3H); MS (+FAB): [M+] m/z 530 (65%), [M+H]+m/z 531 (25%); Anal. calc. for C23H15IO3S2: C, 52.08, H, 2.85, N, 0.00. Found: C, 51.75, H, 2.75, N, 0.06.

Workup

  1. extractionThe organics were extracted with ether (500 mL)
  2. concentrationThe extracts were concentrated

Sources & evidence

ORD record
ord-78fa51f8da9540e0bbe23eefafe1c48f
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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