Pyridine → 1-Bromo-2-isocyanato-4,5-dimethoxybenzene

HRID 539644Notes

Reaction equation

[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[C:19](Cl)(Cl)=[O:20]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[N:4]=[C:19]=[O:20]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Bromo-4,5-dimethoxyaniline (464 mg, 2.0 mmol) was dissolved in 10 ml of toluene at room temperature. DMAP (1 eq, 245 mg), and pyridine (1.3 eq, 0.22 ml) were added followed by phosgene (1.33 eq, 1.33 ml of a 20% solution in toluene). The mixture was heated to 90° C. for 4 hours. Upon cooling, the mixture was filtered and the filtrate was concentrated in vacuo to give 1-bromo-2-isocyanato-4,5-dimethoxy-benzene (542 mg, quantitative) as a light brown oil.

Workup

temperatureUpon cooling
filtrationthe mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-388a648be4cd47a89a630db623166603
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871760B2

Reaction notes

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