Trimethylboroxine → (5-Methyl-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

HRID 1266728Notes

Reaction equation

HRID 1266728 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20])([CH3:4])([CH3:3])[CH3:2].[CH3:23]B1OB(C)OB(C)O1>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([CH3:23])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 574072TrimethylboroxineHCID 69489376(5-Chloro-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 69486745(5-Methyl-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a suspension of (5-chloro-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example A11) (5.00 g, 14.7 mmol) and tetrakis(triphenylphosphine)-palladium in dioxane/water (9:1; 50 ml) was added at RT trimethylboroxine (2.04 ml, 14.7 mmol). The reaction mixture was stirred under reflux conditions for 15 h, filtered, evaporated and purified by column chromatography on silica gel (hexane/ethyl acetate 9:1) to yield a light yellow solid (3.25 g, 69%).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ee72be5f478a445d9b4fd0c13fdfacc0
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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