Methanol → Methyl 4-(allyloxy)-5-bromo-2-chlorobenzoate

HRID 2206694Notes

Reaction equation

HRID 2206694 reaction equation
[CH2:1]([O:4][C:5]1[C:13]([Br:14])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([Cl:15])[CH:6]=1)[CH:2]=[CH2:3].O=S(Cl)Cl.[CH3:20]O>>[CH2:1]([O:4][C:5]1[C:13]([Br:14])=[CH:12][C:8]([C:9]([O:11][CH3:20])=[O:10])=[C:7]([Cl:15])[CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 533294054-(Allyloxy)-5-bromo-2-chlorobenzoic acid

Product 1

HCID 86714037Methyl 4-(allyloxy)-5-bromo-2-chlorobenzoateYield 99%

Conditions

Temperature
0 °C

Procedure

To a solution of compound 21 (17.0 g, 58.0 mmol) in MeOH (380 mL) was added dropwise SOCl2 (21.1 mL, 291 mmol) at 0° C. under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 30 min and then, stirred at 0° C. for 14 hours. The mixture was concentrated in vacuo and poured into aq. saturated NaHCO3 solution and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the crude product 39 (17.7 g, 99%) as a white solid.

Workup

  1. stirringstirred at 0° C. for 14 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionpoured into aq. saturated NaHCO3 solution
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd42639a16ae4904a72be7bf3b771da0
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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