Phosgene → HCID 59408886, compound

HRID 389208Notes

Reaction equation

HRID 389208 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[C:12]([O:17][CH3:18])[CH:11]=1.[C:19](Cl)(Cl)=[O:20]>>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[CH:5][C:6]([C:8]#[N:9])=[CH:7][C:2]=2[N:1]=[C:19]=[O:20])=[CH:11][C:12]=1[O:17][CH3:18]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 594088822-Amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile

Product 1

HCID 59408886HCID 59408886, compoundYield 100%

Procedure

To the product from Step 2 (363 mg, 1.2 mmol) was added phosgene (20% solution in PhMe, 5.9 g, 11.97 mmol), and the mixture was heated to reflux for 2 hours. The solvent was then removed in vacuo to give crude 4′-bromo-2-isocyanato-3′-methoxybiphenyl-4-carbonitrile (394 mg, 1.2 mmol), which was then taken up in chlorobenzene (4 mL). To this mixture, AlCl3 (319 mg, 2.4 mmol) was added at RT. 1 N HCl (30 mL) was then added, which caused a grey precipitate to form. This was isolated by filtration and washed with DCM and MeOH to give the title compound. LRMS (M+H)+=329.0.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-9994fde02f9548c894bef367b6794031
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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