Diethyl Ether → HCID 178516369, compound

HRID 1473511Notes

Reaction equation

HRID 1473511 reaction equation
C[O:2][CH:3]=[C:4]1C(=O)OC(C)(C)O[C:5]1=O.[Br:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[F:22])[NH2:18].C(OCC)C>C1C(Cl)=CC=C(Cl)C=1>[Br:14][C:15]1[CH:16]=[C:17]2[C:19]([C:3]([OH:2])=[CH:4][CH:5]=[N:18]2)=[CH:20][C:21]=1[F:22]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 27792863-Bromo-4-fluoroaniline

Product 1

HCID 178516369HCID 178516369, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

A glass microwave vial was charged with 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Bionet; 0.102 g, 0.552 mmol) and 3-bromo-4-fluoroaniline (Matrix Scientific; 0.100 g, 0.526 mmol) in dichlorobenzene (1.00 ml). The reaction mixture was stirred and heated under microwave irradiation (Biotage AB, Inc., Upssala, Sweden) at 200° C. for 10 min. Diethyl ether was added to the reaction and the solids were filtered, washing well with ether (some product passed through with the filtrate) to yield 61 mg of crude 7-bromo-6-fluoroquinolin-4-ol. Material carried forward without further purification. m/z (ESI) 243.9 (M+H)+.

Workup

  1. filtrationthe solids were filtered
  2. washwashing well with ether (some product

Sources & evidence

ORD record
ord-44eeaf92f0d44b4c933ed01a5b5f2561
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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