1,2-Dibromoethane → 1-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

HRID 219452

Reaction equation

HRID 219452 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([C:23](=[O:25])[CH3:24])[C:5]([OH:22])=[C:6]([O:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])[C:7]=1[O:8][CH3:9].[Br:27][CH2:28][CH2:29]Br>>[Br:27][CH2:28][CH2:29][O:22][C:5]1[C:6]([O:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[C:3]([CH3:26])[C:4]=1[C:23](=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 78391,2-DibromoethaneHCID 595835101-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-hydroxy-4-methoxy-2-methyl-phenyl}-ethanone

Product 1

HCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Procedure

Example 7c (511 mg, 1.34 mmol) was reacted with 1,2-dibromoethane (20.0 eq.) as described under General Procedure F to afford the title compound (641 mg, quantitative yield) as a light brown oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.96 (m, 2H), 4.26 (t, J=6.2 Hz, 2H), 3.96 (t, J=6.6 Hz, 2H), 3.84 (s, 3H), 3.49 (t, J=6.2 Hz, 2H), 2.99 (m, 1H), 2.50 (s, 3H), 2.19 (s, 3H), 2.07-2.01 (m, 2H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 487.3 (M+H+).

Sources & evidence

ORD record
ord-781b40a6dd5d48bfb7bf70ec8a99be46
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Linked notes

Loading…