Methyl Salicylate → HCID 68630037, compound

HRID 2109904Notes

Reaction equation

HRID 2109904 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12](F)[CH:13]=1.[OH:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C(Cl)[Cl:30]>CN(C=O)C>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=1[O:18][C:10]1[CH:9]=[CH:8][CH:13]=[C:12]([Cl:30])[C:11]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 4133Methyl SalicylateHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 68630037HCID 68630037, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (1.30 g, 4 mmol) was added to a mixture of 5-chloro-2-nitrofluorobenzene (352 mg, 2 mmol) and methyl 2-hydroxybenzoate (0.52 mL, 4 mmol) in DMF (6 mL) and the resulting mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with water, dried (Na2SO4), concentrated and flash chromatographed (SiO2, heptane:EtOAc, 10:1-4:1) to give 505 mg (82%) of the title compound (189JO29A). 1H NMR (CDCl3) δ 8.02 (dd, 1 H, J=1.8, 7.8 Hz), 7.96 (d, 1 H, J=1.9 Hz), 7.59 (dt, 1 H, J=2.0, 7.6 Hz), 7.39 (dd, 1 H, J=2.5, 9.0 Hz), 7.24 (dt, 1 H, J=1.2, 7.6 Hz), 7.13 (dd, 1 H, J=1.2, 8.0 Hz), 6.74 (d, 1 H, J=9.0 Hz), 3.77 (s, 3 H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customflash chromatographed (SiO2, heptane:EtOAc, 10:1-4:1)

Sources & evidence

ORD record
ord-45bd5fa7502b4127959570e7ab62dc94
Source dataset
uspto-grants-2009_04
Patent number
US07517871B2

Reaction notes

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