Oxalyl chloride → HCID 59760053, compound

HRID 1879127Notes

Reaction equation

HRID 1879127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]([CH:18]=2)[C:15](O)=[O:16])[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C([Cl:23])=O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]([CH:18]=2)[C:15]([Cl:23])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 59760044HCID 59760044, compound

Product 1

HCID 59760053HCID 59760053, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

DMF (1 drop) was added to a suspension of 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoic acid from the preparation of Intermediate 85 as described above (200 mg, 0.72 mmol) and oxalyl chloride (95 ul, 1.08 mmol, 1.5 eq) in DCM (5 ml). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was then evaporated to dryness and azeotroped with toluene (2×50 ml). The organic layer was separated, dried and evaporated in vacuo to afford the title compound as a yellow solid, 213 mgs. No further purification carried out. LCMS sample dissolved in methanol, MS (ES+) m/z 291 [M+H]+ (C16H1535ClO3), corresponding to methyl ester generated from acid chloride.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customazeotroped with toluene (2×50 ml)
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d944e4fbab88449a94328e35cc37b5f9
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

Loading…