t-Butyl bromide → Tert-butyl 2-nitro-4-phenoxybenzoate

HRID 1673349

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[C:8]([CH3:11])([CH3:10])[CH3:9].CN(C)C(=O)C.[N+:18]([C:21]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])([O-:20])=[O:19]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[N+:18]([C:21]1[CH:29]=[C:28]([O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:27]=[CH:26][C:22]=1[C:23]([O:25][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:24])([O-:20])=[O:19]

Participants

Conditions

Temperature: 55 °C

Procedure

9.9 g of potassium carbonate, 0.82 g of benzyltriethyl-ammonium chloride and 21 mL of 2-bromo-2-methylpropane were added to 14 mL of N,N-dimethylacetamide solution containing 0.93 g of 2-nitro-4-phenoxybenzoic acid at room temperature and stirred at 55° C. for 18 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure to obtain 0.86 g of tert-butyl 2-nitro-4-phenoxybenzoate as white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
washafter washed with a saturated sodium hydrogen carbonate aqueous solution, 10% citric acid aqueous solution
customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-9b0ee9658cf344ea805af8881975cceb
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999132B2

Linked notes

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