4-Chloroguaiacol → Methyl 5-bromo-4-(4-chloro-2-methoxyphenoxy)-2-fluorobenzoate

HRID 1620332Notes

Reaction equation

HRID 1620332 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[Br:11][C:12]1[C:13](F)=[CH:14][C:15]([F:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]>>[Br:11][C:12]1[C:13]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:9][CH3:10])=[CH:14][C:15]([F:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

3

Reactant 2

HCID 280504-ChloroguaiacolHCID 18007754Methyl 5-bromo-2,4-difluorobenzoate

Product 1

HCID 66666661Methyl 5-bromo-4-(4-chloro-2-methoxyphenoxy)-2-fluorobenzoateYield 41.5%

Procedure

Prepared according to Preparation 3 with 4-chloro-2-methoxyphenol (0.13 mL, 1.07 mmol) and methyl 5-bromo-2,4-difluorobenzoate (Preparation 18, 255 mg, 1.02 mmol) at room temperature for 18 hours. The crude product was purified by silica gel chromatography eluting with 5% EtOAc in Heptane to afford the title compound as a white solid (0.165 g).

Workup

  1. customPrepared
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with 5% EtOAc in Heptane

Sources & evidence

ORD record
ord-166e064fbfbb4466a372350af681baad
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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