p-Fluoronitrobenzene → 4,4,5,5-Tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane

HRID 446285Notes

Reaction equation

HRID 446285 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[O:3]1.C(=O)([O-])[O-].[K+].[K+].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[O:5]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 667316814,4,5,5-Tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (2.00 g, 9.09 mmol) in DMF was added Potassium carbonate (2.51 g, 18.2 mmol) and 1-fluoro-4-nitrobenzene (0.964 ml, 9.09 mmol). The reaction was flushed with nitrogen, sealed, and heated to 120 deg. C. After 18 h, water was added and the mixture extracted twice with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purify by silica gel chromatography, eluting with 0-15% EtOAc/hexanes to give 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane as a white solid. MS m/z=342 [M+1]+. Calc'd for C18H20BNO5: 341.17.

Workup

  1. customThe reaction was flushed with nitrogen
  2. customsealed
  3. temperatureheated to 120 deg. C
  4. additionwater was added
  5. extractionthe mixture extracted twice with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurify by silica gel chromatography
  10. washeluting with 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-414844f8418840c496762d11e3c86bb1
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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