Ethyl Acetate → HCID 58160187, compound

HRID 1425576Notes

Reaction equation

HRID 1425576 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-:22])([O-])=O.[Na+].[Na+].CCO[C:28]([CH3:30])=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:30]2[CH:28]=[CH:12][C:11]([NH:16][CH:19]=[O:22])=[CH:10][CH:9]=2)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 110436225-Benzyloxy-2-chloro-nitrobenzene

Product 1

HCID 58160187HCID 58160187, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 4-(benzyloxy)-1-chloro-2-nitrobenzene (394 mg, 1.5 mmol) N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide (370 mg, 1.5 mmol) in 6 mL dioxane was added 3 mL of a 1 M Na2CO3 (aq) solution and Tetrakis(triphenylphosphine)palladium (52 mg, 0.045 mmol). The suspension was headed at reflux for 15 h under Ar atmosphere and cooled to rt. It was added EtOAc (80 mL) and washed with brine (50 mL), water (2×80 mL), and dried over MgSO4. After solvent removal, the residue was chromatographed (hexane/EtOAc) to afford N-(4′-(benzyloxy)-2′-nitrobiphenyl-4-yl)formamide as a yellow solid (395 mg, 75%). MS (ESI) m/z 349 (M+H+).

Workup

  1. temperatureat reflux for 15 h under Ar atmosphere
  2. washwashed with brine (50 mL), water (2×80 mL)
  3. dry with materialdried over MgSO4
  4. customAfter solvent removal
  5. customthe residue was chromatographed (hexane/EtOAc)

Sources & evidence

ORD record
ord-84963999837c4cda97ffa3402f7077fa
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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