2-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenol → HCID 9916610, compound

HRID 1954289Notes

Reaction equation

HRID 1954289 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[O:17][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([CH2:23][CH3:24])[C:3]=1[OH:25].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]>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[O:17][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([CH2:23][CH3:24])[C:3]=1[O:25][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]

Participants

3

Reactant 2

HCID 101787952-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenolHCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 9916610HCID 9916610, compoundYield 23.9%

Procedure

The title compound was prepared according to the procedure in Example 1, step 9, using 2-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenol (0.458 g, 1.16 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.994 g, 4.19 mmol). Purification on 2% H3PO4 /MeOH treated silica gel eluting with a 0 & 10% EtOAc/hexane step gradient gave 0.165 g of the title compound as a white solid, mp 238-243° C. 1H NMR (DMSO-d6) δ 1.13 (t, 3 H), 1.56 (s, 3 H), 2.39 (s, 3 H), 2.65-2.70 (m, 2 H), 7.37-7.60 (m, 7 H), 8.01-8.08 (m, 3 H). mass spectrum (-ESI) m/z 593 (M-H). Anal. Calcd. for C29H23BrO7S: C, 58.50; H, 3.89; N, 0.00. Found: C, 58.91; H, 4.02; N, 0.05.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4 /MeOH
  3. additiontreated silica gel eluting with a 0 & 10% EtOAc/hexane step gradient

Sources & evidence

ORD record
ord-9758c3ce1ca74d6ab7743c9617ab17c8
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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