Water → 4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

HRID 20035

Reaction equation

HRID 20035 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.O.Cl[C:11]([CH3:15])([CH3:14])[C:12]#[CH:13]>[Cu].[Cu]Cl.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:11]([CH3:15])([C:12]#[CH:13])[CH3:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962Water2×HCID 78074-BromoanilineHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 200822714-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-bromobenzenamine (4.0 g, 23 mmol), TEA (4.3 ml, 31 mmol), 2.0 ml of water, copper (0.058 g, 0.91 mmol) and copper(I) chloride (0.058 g, 0.59 mmol) in diethyl ether (9.8 ml, 20 mmol) was added 3-chloro-3-methylbut-1-yne (2.0 g, 20 mmol), dropwise. After stirring overnight, the reaction mixture was transferred to a seperatory funnel containing water and diethyl ether. The aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated. The crude oil was purified with by MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH)) to provide the product as an oil. MS m/z: 240 (M+2).

Workup

  1. customthe reaction mixture was transferred to a seperatory funnel
  2. washThe aqueous layer was washed 3× with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified with by MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))

Sources & evidence

ORD record
ord-84f384e1b4ca4b4897235a5af4920794
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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