tert-Butanol → 2-(2-Chlorophenylamino)-3,4-difluoro-6-formylbenzoic acid methyl ester

HRID 1723691Notes

Reaction equation

HRID 1723691 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[C:9]([CH:10]=CC2C=CC=CC=2)=[CH:8][C:7]([F:18])=[C:6]([F:19])[C:5]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27].CC([OH:33])(C)C.C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[C:9]([CH:10]=[O:33])=[CH:8][C:7]([F:18])=[C:6]([F:19])[C:5]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 865985952-(2-Chlorophenylamino)-3,4-difluoro-6-styrylbenzoic acid methyl ester

Product 1

HCID 865985962-(2-Chlorophenylamino)-3,4-difluoro-6-formylbenzoic acid methyl esterYield 755.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-6-styrylbenzoic acid methyl ester (1.20 g, 3.00 mmol), 2.5% OSO4 solution in t-BuOH (2.0 mL, 0.165 mmol) and NMO (0.435 g, 3.60 mmol) in 30 mL of 1:1 THF/water was stirred for 1 hour. Sodium periodate (0.963 g, 4.50 mmol) was added. After 1 hour, the reaction mixture was diluted with ethyl acetate and water and the layers separated. The organic layer was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography (1:1 methylene chloride/hexanes) gave 0.406 g (42%) pure desired product.

Workup

  1. waitAfter 1 hour
  2. customthe layers separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (1:1 methylene chloride/hexanes)

Sources & evidence

ORD record
ord-1bbd2f881432432ba73b368f5f87016c
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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