4-Methyl-2,6-dimethoxyphenol → 2-[3-(4-Fluorophenyl)butoxy]-1,3-dimethoxy-5-methylbenzene

HRID 219449Notes

Reaction equation

HRID 219449 reaction equation
Br[CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH3:5].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH3:24])[CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[OH:21]>>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[CH2:3][CH2:2][O:21][C:20]2[C:19]([O:22][CH3:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=2[O:14][CH3:13])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 2409254-Methyl-2,6-dimethoxyphenolHCID 592724301-(4-Bromobutan-2-yl)-4-fluorobenzene

Product 1

HCID 595835092-[3-(4-Fluorophenyl)butoxy]-1,3-dimethoxy-5-methylbenzeneYield 82%

Procedure

Example 4a (2.54 g, 11 mmol) and 3,5-dimethoxy-4-hydroxy-toluene (1.68 g, 10 mmol) were reacted as described under General Procedure A and the crude product was purified by flash chromatography (silica-gel, hexane/EtOAc 19:1) to provide the product as a clear oil (2.6 g, 82%). 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 6.97-6.91 (m, 2H), 6.35 (s, 2H), 3.85-3.37 (m, 8H), 3.10-3.02 (m, 1H), 3.28 (s, 3H), 2.04-1.89 (m, 2H), 1.26 (d, J=6.9 Hz, 3H).

Workup

  1. customthe crude product was purified by flash chromatography (silica-gel, hexane/EtOAc 19:1)

Sources & evidence

ORD record
ord-9fc27a34e2774e28b80849c2f23f05f7
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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