Methanol → Methyl 3-bromo-2,6-dimethoxybenzoate

HRID 722779

Reaction equation

HRID 722779 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.CO.[CH2:21](N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:5]([O:7][CH3:21])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27747443-Bromo-2,6-dimethoxybenzoic acid

Product 1

HCID 21886016Methyl 3-bromo-2,6-dimethoxybenzoateYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromo-2,6-dimethoxybenzoic acid (5.0 g, 19.2 mmol) and thionyl chloride (10 ml) were heated to reflux for 2 h. The mixture was then concentrated in vacuo and diluted with CH2Cl2 (20 ml) and added to a solution of MeOH (614 mg, 38.4 mmol) and triethylamine (3.88 g, 38.4 mmol) in CH2Cl2 (100 ml) at 0° C. The resulting mixture was allowed to warm to RT and stirred for 64 h. The organics were washed with 10% HCl (50 ml), brine (50 ml) and dried (MgSO4) and purified by chromatography (0–50% EtOAC in heptane) to leave a white solid (4.17 g).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. additiondiluted with CH2Cl2 (20 ml)
  4. washThe organics were washed with 10% HCl (50 ml), brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. custompurified by chromatography (0–50% EtOAC in heptane)

Sources & evidence

ORD record
ord-6457be78d84249448fa0ee2b08f904df
Source dataset
uspto-grants-2006_11
Patent number
US07138527B2

Linked notes

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