Potassium Bromide → 4-{4-[2-(2-Benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenoxysulfonyl}-2-hydroxy-benzoic acid

HRID 1067344Notes

Reaction equation

HRID 1067344 reaction equation
[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:27]([C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[C:32]([OH:39])[CH:31]=1)(=[O:29])=[O:28].[K+].[Br-]>>[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][S:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[C:32]([OH:39])[CH:31]=2)(=[O:29])=[O:28])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 234456124-[2-(2-Benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenol

Product 1

HCID 101873284-{4-[2-(2-Benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenoxysulfonyl}-2-hydroxy-benzoic acid

Procedure

The title compound was prepared according to the procedure in Example 4 using 4-[2-(2-benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenol (0.400 g, 1.16 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.550 g, 2.32 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 20% EtOAc/hexane gave the tide compound as an off white solid, mp 57-59° C. 1H NMR (DMSO-d6) δ2.74 (t, 2H), 3.09 (t, 2H), 4.00 (s, 2H), 6.97 (d, 2H), 7.19-7.23 (m, 5H), 7.27-7.38 (m, 6H), 7.76 (d, 1H), 7.83 (dd, 1H), 7.98 (d, 1H). IR (KBr) 3400, 2950, 1675, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 543 (M−H).

Workup

  1. customPurification on 2% H3PO4/MeOH
  2. additiontreated silica gel
  3. washeluting with 20% EtOAc/hexane
  4. customgave the tide compound as an off white solid, mp 57-59° C

Sources & evidence

ORD record
ord-ddf0544a1b1442359e787fe4040e57b5
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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