Triphosgene → 1-bromo-4-((1R)-1-isocyanatoethyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:11])[CH2:9]C)=[CH:4][CH:3]=1.[C:12]([O-])(O)=[O:13].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:11]=[C:12]=[O:13])[CH3:9])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-1-(4-bromophenyl)propan-1-amine (5 g, 25 mmol) in CH2Cl2 (10 mL) was added saturated aqueous NaHCO3 (10 mL) and then triphosgene (2.45 g, 8 mmol) at 0. Then the reaction mixture was stirred for 15 minutes at 0° C. under nitrogen. The reaction mixture was extracted with CH2Cl2 twice. The combined organic phases were dried over Na2SO4, filtered and concentrated to afford (R)-1-bromo-4-(1-isocyanatoethyl)benzene (2.5 g, 44%), which was used for the next step without purification.
Workup
- extractionThe reaction mixture was extracted with CH2Cl2 twice
- dry with materialThe combined organic phases were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-864d8dd566ed44d48d5882761813cc5d
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487094B2
Reaction notes
Loading…