Thiophosgene → 1,3-Dibromo-2-isothiocyanato-5-methoxybenzene

HRID 1628561Notes

Reaction equation

HRID 1628561 reaction equation
[C:1](Cl)(Cl)=[S:2].[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([Br:15])[C:7]=1[NH2:8]>O1CCCC1.C(=O)([O-])O.[Na+]>[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([Br:15])[C:7]=1[N:8]=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 5428952,6-Dibromo-4-methoxyaniline

Product 1

HCID 866329141,3-Dibromo-2-isothiocyanato-5-methoxybenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Thiophosgene (1.52 mL, 20.5 mmol) was added dropwise to a stirred mixture of 2,6-dibromo-4-methoxyaniline (2.86 g, 10.2 mmol) in tetrahydrofuran (25 mL) and saturated aqueous sodium hydrogen carbonate (25 mL) at 0° C. The mixture was stirred at room temperature for 1 h, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (3.22 g, 9.97 mmol, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f46ddcef837748bdbbace9d9f9044def
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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