Boron tribromide → 2-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenol

HRID 1954288Notes

Reaction equation

[CH2:1]([C:8]1[O:9][C:10]([CH3:27])=[C:11]([CH3:26])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([O:23]C)=[C:17]([Br:25])[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[Br:25][C:17]1[CH:16]=[C:15]([C:13]2[C:12]3[C:11]([CH3:26])=[C:10]([CH3:27])[O:9][C:8]=3[CH:1]=[C:2]3[C:7]=2[CH:6]=[CH:5][CH:4]=[CH:3]3)[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]=1[OH:23]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 18430715HCID 18430715, compound

Product 1

HCID 101787952-bromo-4-(2,3-dimethyl-naphtho[2,3-b]furan-4-yl)-6-ethyl-phenolYield 12%

Procedure

The title compound was prepared according to the procedure in Example 1, step 5, using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3-bromo-5-ethyl-4-methoxy-phenyl)-methanone (7.85 g, 18.4 mmol) and boron tribromide (13.2 mL, 0.139 mol). Purification on silica gel eluting with 2% EtOAc/hexane, followed by trituration with hexane gave 0.85 g (12%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 1.15 (t, 3 H), 1.59 (s, 3 H), 2.37 (s, 3 H), 2.64-2.77 (m, 2 H), 7.09 (d, 1 H), 7.31 -7.35 (m, 2 H), 7.42 (d of t, 1 H), 7.52 (d, 1 H), 7.95 (s, 1 H), 7.99 (d, 1 H), 9.17 (s, 1 H). mass spectrum (EI) m/z 394 (M+). Anal. Calcd. for C22H19Br1O2 : C, 66.85; H, 4.84; N, 0.00. Found: C, 67.07; H, 4.85, N, 0.05.

Workup

customThe title compound was prepared
customPurification on silica gel eluting with 2% EtOAc/hexane

Sources & evidence

ORD record: ord-7cc543a2aed34a1280c85b7dc3b2a3ab
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

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