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

HRID 219465Notes

Reaction equation

HRID 219465 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][CH2:30]Br>>[Br:27][CH2:28][CH2:29][CH2:30][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 80011,3-DibromopropaneHCID 595835101-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-hydroxy-4-methoxy-2-methyl-phenyl}-ethanone

Product 1

HCID 595835011-{2-(3-Bromo-propoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Procedure

Example 7c (179 mg, 0.47 mmol) was reacted with 1,3-dibromopropane (10.0 eq.) as described under General Procedure F to afford the title compound (641 mg, quantitative yield) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.19-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.10 (t, J=5.9 Hz, 2H), 3.94 (t, J=6.7 Hz, 2H), 3.84 (s, 3H), 3.49 (t, J=6.5 Hz, 2H), 2.99 (m, 1H), 2.46 (s, 3H), 2.17 (m, 5H), 2.07-1.99 (m, 2H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 503.0 (M+H+)

Sources & evidence

ORD record
ord-db02bcb5a350424eac375ac114f818da
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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