4-Bromophenol → HCID 90332535, compound

HRID 595588Notes

Reaction equation

[CH:1]1([C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.CC.[Cl].[Cl]>>[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[O:11][C:4]([CH:1]3[CH2:3][CH2:2]3)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:17]=2[CH:18]=1

Participants

Reactant 3

HCID 78084-Bromophenol

HCID 262979Ethyl 3-cyclopropyl-3-oxopropanoate

HCID 178456127HCID 178456127, compound

Product 1

HCID 90332535HCID 90332535, compoundYield 21%

Conditions

Temperature: 80 °C

Procedure

(t-BuO)2 (94 g, 640 mol) was added to a solution of ethyl 3-cyclopropyl-3-oxopropanoate (50 g, 320 mmol), 4-bromophenol (166 g, 9.6 mol) and FeCl.6H2O (5.8 g, 32 mmol) in Di-chlorine Ethane (316 g, 3.2 mol) under N2 gas at 25° C. The mixture was stirred at 80° C. for 6 hours. The solvent was removed and the residue was purified by column chromatography (eluted with PE:EA from 20:1 to 10:1) to furnish the pure product of ethyl 5-bromo-2-cyclopropylbenzofuran-3-carboxylate (20.0 g, yield: 21%). 1H-NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.30 (d, J=7.2 Hz, 1H), 7.18 (d, J=7.2 Hz, 1H), 4.42 (q, J=7.2 Hz, 2H), 3.01˜3.05 (m, 1H), 1.44 (t, J=7.2 Hz, 3H), 1.24˜1.26 (m, 2H), 1.16˜1.19 (m, 2H). MS (M+H)+: 309/311.

Workup

customThe solvent was removed
customthe residue was purified by column chromatography (eluted with PE:EA from 20:1 to 10:1)

Sources & evidence

ORD record: ord-f9a104db774b4200a6564d4917ab1d6c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242998B2

Reaction notes

Loading…