4-(Chlorosulfonyl)-2-hydroxybenzoic acid → HCID 9939622, compound

HRID 1954272Notes

Reaction equation

HRID 1954272 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:26])=[C:19]([CH:27]([CH3:29])[CH3:28])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.Cl[S:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=1)(=[O:33])=[O:32]>>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH:23]([CH3:24])[CH3:25])[C:20]([O:26][S:31]([C:34]3[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=3)(=[O:33])=[O:32])=[C:19]([CH:27]([CH3:29])[CH3:28])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 18430704HCID 18430704, compound

Product 1

HCID 9939622HCID 9939622, compound

Procedure

Using 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-diisopropyl-phenol (0.291 g, 0.623 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.768 g, 3.24 mmol) the title compound was prepared according to the procedure in Example 1, step 9. Purification on Dynamax C18 eluting with 100% CH3CN (0.1% TFA added) gave 0.09 g (22%) of the title compound as a white solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.09 (t, 12 H), 1.54 (s, 3 H), 2.45 (s, 3 H), 3.14-3.22 (m, 2 H), 7.27 (s, 2 H), 7.41-7.46 (m, 2 H), 7.50-7.53 (m, 2 H), 7.65-7.69 (m, 1 H), 8.09 (d, 1 H), 8.21-8.23 (m, 1 H). IR (KBr) 3400, 2950, 1700, 1375 and 1180 cm-1. mass spectrum (-ESI), m/z 665/667 (M-H). Anal. Calcd. for C33H31BrO6S2.1.7H2O: C, 56.76; H, 4.97 N, 0.00. Found: C, 56.73; H, 4.81 N, 0.12.

Sources & evidence

ORD record
ord-ae3b65904ae545f480a7d3271be3fb10
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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