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

HRID 2193449Notes

Reaction equation

HRID 2193449 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□. 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-3717aeaea7174dffbbc683b3b3bcd9c9
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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