Triethylamine → HCID 11535972, compound

HRID 1241930Notes

Reaction equation

HRID 1241930 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 11535972HCID 11535972, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the 4-fluoro-3-nitroaniline (5.00 g, 32.03 mmol), phenylboronic acid (7.81 g, 64.05 mmol), copper(II) acetate (5.82 g, 32.03 mmol) and 4 Å molecular sieves (5.00 g) in dichloromethane (200.0 mL) and triethylamine (22.3 mL, 160 mmol) was placed in a round bottomed flask. The resulting suspension was stirred at room temperature under a dry ambient atmosphere for 48 h. The mixture was filtered through diatomaceous earth and the solvent was removed via rotary evaporation. The resulting residue was re-dissolved in EtOAc, adsorbed on silica gel and flash chromatographed (15% EtOAc/hexanes) to give 4-fluoro-3-nitro-N-phenylaniline as an orange solid (5.24 g, 70.5 % yield). M−, 231.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe solvent was removed via rotary evaporation
  3. dissolutionThe resulting residue was re-dissolved in EtOAc
  4. customchromatographed (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b4be979fd6854634bce2b3d122be107a
Source dataset
uspto-grants-2006_10
Patent number
US07115644B2

Reaction notes

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