Dimethylformamide → Diethylphosphonomethyl 4-chloro-2-methoxybenzoate

HRID 2222112

Reaction equation

HRID 2222112 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.C(N(CC)CC)C.O[CH2:32][P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:32][P:33]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])=[O:40])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 76513Diethyl phosphonomethanolHCID 936824-Chloro-o-anisic acid

Product 1

HCID 57457786Diethylphosphonomethyl 4-chloro-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 4-chloro-2-methoxybenzoic acid (1 mmol), oxalyl chloride (1 mmol), and DMF (0.05 mmol) in 2 mL of CH2Cl2 was stirred at rt for 6 h and then evaporated. To the residue was added 2 mL of CH2Cl2, triethylamine (2 mmol) and diethyl (hydroxymethyl)phosphonate (0.33 mmol) and this mixture was stirred at rt for 16 h and then diluted with water and CH2Cl2. The organic layer was dried (MgSO4) and evaporated. Purification of the residue by silica gel chromatography provided diethylphosphonomethyl 4-chloro-2-methoxybenzoate as an oil.

Workup

  1. customevaporated
  2. stirringthis mixture was stirred at rt for 16 h
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-7e4e9ff495a54311b5a7cda48e9bc141
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Linked notes

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