3-Nitrophenylboronic Acid → HCID 59804338, compound

HRID 422003Notes

Reaction equation

HRID 422003 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 8471TriethylamineHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 59804338HCID 59804338, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A round bottom flask is charged with 3-nitrophenylboronic acid (4.2 g, 25 mmol), dry molecular sieves (5 g), copper acetate (1.95 g, 12.5 mmol) and dry dichloromethane (150 mL). Triethylamine (8.7 mL, 62.5 mmol) is added followed by the addition of 4-fluoro-3-nitroaniline (2.27 g, 12.5 mmol). The resulting mixture is stirred at ambient temperature for three days. The mixture is filtered through celite and washed with EtOAc. The filtrate is concentrated and purified by column chromatography (EtOAc/Hexane=1:3) to give the desired product: 1H NMR (400 MHz, DMSO) δ 9.12 (s, 1 H), 7.82 (m, 1 H), 7.79-7.37 (m, 1 H), 7.73-7.70 (m, 1 H), 7.56-7.49 (m, 4 H); LC-MS: 278.3 (MH+).

Workup

  1. filtrationThe mixture is filtered through celite
  2. washwashed with EtOAc
  3. concentrationThe filtrate is concentrated
  4. custompurified by column chromatography (EtOAc/Hexane=1:3)

Sources & evidence

ORD record
ord-17eb5aba3e6c4901955cf0e49a93423f
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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