4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(2-Butyl-benzofuran-3-ylmethyl)-phenoxysulfonyl]-2-hydroxy-benzoic Acid

HRID 1067378Notes

Reaction equation

HRID 1067378 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].Cl[S:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[C:28]([OH:35])[CH:27]=1)(=[O:25])=[O:24]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][S:23]([C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[C:28]([OH:35])[CH:27]=2)(=[O:25])=[O:24])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 234456454-(2-Butyl-benzofuran-3-ylmethyl)-phenol

Product 1

HCID 101628454-[4-(2-Butyl-benzofuran-3-ylmethyl)-phenoxysulfonyl]-2-hydroxy-benzoic AcidYield 86%

Procedure

The title compound was prepared according to the procedure in Example 4 using 4-(2-butyl-benzofuran-3-ylmethyl)-phenol (0.500 g, 1.78 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.844 g, 3.56 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with EtOAc/hexane gave 0.728 g (86%) of the title compound as an orange solid, mp 135-138° C. 1H NMR (DMSO-d6) δ0.84 (t, 3H), 1.27 (sextet, 2H), 1.58 (quintet, 2H), 2.76 (t, 2H), 3.97 (s, 2H), 6.96 (d, 2H), 7.10 (dt, 1H), 7.17 (dt, 1H), 7.22-7.31 (m, 5H), 7.43 (d, 1H), 7.95 (d, 1H). IR (KBr) 3300, 2950, 1675, 1390 and 1175 cm−1. mass spectrum (−ESI) m/z 479 (M−H). Anal. Calcd. for C26H24O7S.0.2H2O: C, 64.50; H, 5.08; N, 0.00. Found: C, 64.50; H, 5.07; N, 0.06.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-43f026192f4c4be4b2543acf58a4a1f8
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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