Toluene → HCID 23433644, compound

HRID 1279953Notes

Reaction equation

HRID 1279953 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].Br[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([F:21])[CH:15]=1.C([O-])([O-])=O.[K+].[K+].[C:28]1([CH3:34])[CH:33]=C[CH:31]=[CH:30][CH:29]=1>O.CCOC(C)=O.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>[F:21][C:16]1[CH:15]=[C:14]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:20]=[C:19]2[C:17]=1[NH:18][C:28]([CH3:34])([CH3:33])[CH:29]=[C:30]2[CH3:31]

Participants

8

Reactant 4

HCID 1140TolueneHCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 23433644HCID 23433644, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-nitrobenzeneboronic acid (0.70 g, 4.2 mmol), 4-bromo-2-Fluoroaniline (730 mg, 4.0 mmol), (PPh3)4Pd (93 mg, 0.08 mmol), and K2CO3 (0.69 g, 5.0 mmol) in toluene (20 mL) and water (2 mL) was heated at 95° C. for 16 h and the mixture was diluted with EtOAc (20 mL). The mixture was washed with water (10 mL) and brine (10 mL), concentrated and purified by silica gel chromatography to afford the 4-amino-3-Fluoro-3′-nitrobiphenyl (structure 82 of Scheme XXI, where R1═R3-7=H, R8=F) (0.4 g, 41%) as a yellow solid.

Workup

  1. washThe mixture was washed with water (10 mL) and brine (10 mL)
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a571d700f4cc4f8f9a70937619a99be0
Source dataset
uspto-grants-2002_09
Patent number
US06448405B1

Reaction notes

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