3-Bromoaniline → 4'-Butyl[1,1'-biphenyl]-3-amine

HRID 1690678Notes

Reaction equation

HRID 1690678 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12].[F-].[Cs+]>O1CCOCC1>[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:8]=[CH:7][CH:6]=[C:4]([NH2:5])[CH:3]=2)=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 25953Cesium fluorideHCID 41008604-Butylphenylboronic acid

Product 1

HCID 549123704'-Butyl[1,1'-biphenyl]-3-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A sample of 3-bromoaniline (2.00 g, 11.6 mmol), 4-butylphenylboronic acid (3.1 g, 17.4 mmol) and cesium fluoride (5.3 g, 35 mmol) are charged to a microwave reaction vial and treated with anhydrous dioxane (12 mL) and bis(tri-tert-butylphospine) (600 mg, 1.16 mmol). The vial is sealed and purged with nitrogen for 5 minutes. The reaction is then heated to 120° C. for 5 minutes and filtered over celite washing with ethyl acetate. The solvent was removed and the crude material was purified by UV triggered reverse phase HPLC to afford the title compound: ESMS m/z 226.2 (M+H+).

Workup

  1. customThe vial is sealed
  2. custompurged with nitrogen for 5 minutes
  3. filtrationfiltered
  4. washover celite washing with ethyl acetate
  5. customThe solvent was removed
  6. customthe crude material was purified by UV triggered reverse phase HPLC

Sources & evidence

ORD record
ord-c5e58f5635214421adf47bf3eec5c752
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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