Pyridine → HCID 11106338, compound

HRID 403189Notes

Reaction equation

HRID 403189 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[Cl:11][C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[Cl:11][C:12]([O:10][C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 106982,4,6-TrimethylphenolHCID 94429Triphosgene

Product 1

HCID 11106338HCID 11106338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,4,6-trimethylphenol (272 mg, 2.00 mmol, 1.0 equiv) was dissolved in CH2Cl2 (3.33 mL, 0.3 M) under nitrogen (N2) and cooled to 0° C. Triphosgene (208 mg, 0.700 mmol, 0.35 equiv) was dissolved in CH2Cl2 (3.33 mL) and added dropwise, followed by pyridine (0.162 mL, 2.00 mmol, 1.0 equiv). The mixture was allowed to warm to 25° C. over 18 h, at which point the reaction was quenched with 10 mL 1 normal (N) hydrochloric acid (HCl; aq) and extracted with EtOAc. The organic layer was washed with 1 N HCl (aq), dried over Na2SO4, and concentrated to give mesityl chloroformate as an oil (88% purity by 1H NMR spectroscopy). The chloroformate so prepared was used directly in the next step without further purification.

Workup

  1. additionadded dropwise
  2. temperatureto warm to 25° C. over 18 h, at which
  3. customwas quenched with 10 mL 1 normal (N) hydrochloric acid (HCl; aq)
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with 1 N HCl (aq)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7f16c79fdb704b8cb59efdd24be8459f
Source dataset
uspto-grants-2014_06
Patent number
US08748340B2

Reaction notes

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