Sodium Carbonate → HCID 90419008, compound

HRID 2202375Notes

Reaction equation

HRID 2202375 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:16]([F:21])([F:20])C([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[F:20][CH:16]([F:21])[O:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 139539Salicylic acid, 4-nitro-, methyl esterHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 90419008HCID 90419008, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-hydroxy-4-nitrobenzoate (1.1 g, 5.6 mmol), sodium 2-chloro-2,2-difluoroacetate (1.0 g, 6.6 mmol) and Na2CO3 (710 mg, 6.7 mmol) in DMF (10 mL) was stirred at 100° C. overnight. After cooling to rt, the mixture was partitioned between water and EtOAc. The organic layer was separated and washed with twice with water, then brine, dried over Na2SO4 and concentrated, and purified by a standard method to give the title product (330 mg). 1H NMR (CHLOROFORM-d) δ: 8.15-8.19 (m, 1H), 8.13 (s, 1H), 8.06 (d, J=8.6 Hz, 1H), 6.68 (s, 1H), 3.98 (t, J=72.8 Hz, 1H).

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. washwashed with twice with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by a standard method

Sources & evidence

ORD record
ord-d936b61027754d9f8f512cd4dbbf3f4d
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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