2-Bromoethanol → 1-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-(2-hydroxy-ethoxy)-4-methoxy-2-methyl-phenyl]-ethanone

HRID 219461Notes

Reaction equation

HRID 219461 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[CH2:28][CH2:29][OH:30]>>[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([C:23](=[O:25])[CH3:24])[C:5]([O:22][CH2:28][CH2:29][OH:30])=[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]

Participants

3

Reactant 2

HCID 108982-BromoethanolHCID 595835101-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-hydroxy-4-methoxy-2-methyl-phenyl}-ethanone

Product 1

HCID 595835021-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-(2-hydroxy-ethoxy)-4-methoxy-2-methyl-phenyl]-ethanoneYield 67%

Procedure

Example 7c (93 mg, 0.24 mmol) was reacted with 2-bromoethanol (1.5 eq.) as described under General Procedure F and the crude mixture was purified by flash chromatography (silica gel, Et2O/hexane 70:30) to afford the title compound (68 mg, 67%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.19-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.13-4.11 (m, 2H), 3.95 (d, J=6.8 Hz, 2H), 3.84 (s, 3H), 3.76-3.70 (m, 2H), 3.00 (m, 1H), 2.80 (t, J=6.5 Hz, 1H), 2.50 (s, 3H), 2.20 (s, 3H), 2.06-1.98 (m, 2H), 1.29 (d, J=6.9 Hz, 3H). MS (ES+) m/z 425.2 (M+H+).

Workup

  1. customthe crude mixture was purified by flash chromatography (silica gel, Et2O/hexane 70:30)

Sources & evidence

ORD record
ord-b02b600d90c444e28bbdf3554dd3d52c
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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