1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 86698330, compound
Reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.C(O[K])(C)(C)C.[CH3:16][N:17]([CH3:22])[CH2:18][CH2:19][NH:20]C>C1(C)C=CC=CC=1>[Br:9][C:4]1[CH:3]=[C:2]([NH:20][CH2:19][CH2:18][N:17]([CH3:22])[CH3:16])[CH:7]=[C:6]([F:8])[CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 1,3-dibromo-5-fluorobenzene (LXXIV) (4 g, 15.75 mmol) in toluene (50 mL) was added tBuOK (5.3 g, 47.25 mmol) and N1,N1,N2-trimethylethane-1,2-diamine (2.778 mL, 31.5 mmol). The reaction was stirred at 110° C. overnight. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3→5:95 MeOH:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (LXXV) as a brown viscous oil (1.02 g, 3.91 mmol, 24.8% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 2.17 (s, 6H), 2.40 (t, J=3.5 Hz, 2H), 3.01-3.09 (m, 2H), 6.10 (t, J=5 Hz, 1H), 6.38 (dt, J=12 Hz, J=2 Hz, 1H), 6.51 (dt, J=8.5 Hz, J=2 Hz, 1H), 6.60 (s, 1H); ESIMS found C12H16BrFN2 m/z 261 (M+H).
Workup
- customThe solvent was removed under vacuum
- customthe residue was partitioned between EtOAc and water
- customThe organic layer was separated
- washwashed with water, brine
- dry with materialdried over MgSO4
- customevaporated under vacuum
- customThe crude product was purified on a silica gel column (100% CHCl3→5:95 MeOH:CHCl3)
Sources & evidence
- ORD record
- ord-924a1ca699604ab3ba6f2a6662b0cd6c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673936B2
Reaction notes
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