Sodium Carbonate → 4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine
Reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)=[C:10]([CH3:9])[CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
A mixture of 4-iodo-aniline (25.0 g, 114.1 mmol), 2-methyl-4-chlorophenyl-boronic acid (29.17 g, 171.1 mmol), PdCl2(P(o-tolyl)3)2 (11.66 g, 14.8 mmol), and Na2CO3 (60.49 g, 570.7 mmol) in DME/EtOH/H2O (100/50/25 mL) was heated 125° C. for 2 h. The reaction mixture was cooled to room temperature, filtered and washed with EtOAc (200 mL). The solvent was removed under reduced pressure. The crude mixture was extracted with ethyl acetate (500 mL) and the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel, eluting with 5-30% Hexane/EtOAc to afford 4′-Chloro-2′-methyl biphenyl-4-ylamine. 1H NMR (300 MHz, CDCl3): δ 7.24-7.08 (m, 5 H), 6.72 (d. J=7.2 Hz, 2 H), 3.70 (bs, 2 H), 2.27 (s, 3 H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- washwashed with EtOAc (200 mL)
- customThe solvent was removed under reduced pressure
- extractionThe crude mixture was extracted with ethyl acetate (500 mL)
- washthe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting crude was purified by column chromatography on silica gel
- washeluting with 5-30% Hexane/EtOAc
Sources & evidence
- ORD record
- ord-a6ab28a8dce341ad8d9760561ccdfb65
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08907103B2
Reaction notes
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