Dimethylformamide → HCID 10806074, compound

HRID 983791Notes

Reaction equation

HRID 983791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([I:12])[C:5](O)=[C:6]([CH:10]=1)C(O)=O.[C:13]([O-:16])([O-])=[O:14].[K+].[K+].I[CH3:20].CN([CH:24]=[O:25])C>CCOCC>[CH3:20][O:16][C:13](=[O:14])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]([I:12])[C:5]=1[O:25][CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 929387HCID 929387, compound

Product 1

HCID 10806074HCID 10806074, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Chloro-2-hydroxy-3-iodo-benzoic acid 41 in DMF (40 mL) was treated with K2CO3 (5.70 g, 41 mmol) and then stirred for 15 min. The mixture was chilled to 0° C. under nitrogen and iodomethane (2.82 mL, 45 mmol) was added. This heterogeneous mixture was stirred for 18 h at 20° C. Additional K2CO3 (0.57 g, 4.1 mmol) and iodomethane (0.28 mL, 4.5 mmol) were added. After 6 h, the mixture was diluted with ether, washed with saturated NaHCO3, NaCl, and dried (Na2SO4). The solvent was removed under reduced pressure to give 5-Chloro-3-iodo-2-methoxybenzoic acid methyl ester 42 as a light purple crystalline solid (6.21 g, 93% yield).

Workup

  1. stirringThis heterogeneous mixture was stirred for 18 h at 20° C
  2. waitAfter 6 h
  3. washwashed with saturated NaHCO3, NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a0b3f0b262bc486c8ea9e853c2e86608
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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