Triphosgene → 1-bromo-4-((1R)-1-isocyanatoethyl)benzene

HRID 2037545Notes

Reaction equation

HRID 2037545 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]=1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 7127717(S)-1-(4-bromophenyl)propan-1-amine

Product 1

HCID 70182821-bromo-4-((1R)-1-isocyanatoethyl)benzeneYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 μl. 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

  1. extractionThe reaction mixture was extracted with CH2Cl2 twice
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f40ee846b7584d3db91e80a070d0e459
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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