3-Chlorophenol → HCID 9948853, compound

HRID 863411Notes

Reaction equation

HRID 863411 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1.CCOC(C)=O>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 9948853HCID 9948853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

THF (5 ml) and NaH (60% disp in oil, approx. 28 mg) is added to a dry flask maintained under inert atmosphere at room temperature. 3-Chlorophenol (0.09 g) is added as a soln. in THF (1 mL) and stirring is continued until the solution became clear. 4-Chloro-6,7-dimethoxyquinazoline is added all at once (as the solid) and stirring was maintained overnight at RT. The solution is partitioned between CH2Cl2 and 5% NaOH. The organic layer is washed with brine, dried (Na2SO4) and concentrated. Flash column chromatography (40% EtOAc/Hex) provided the pure compound. An analytical sample is obtained by recrystallization from EtOAc/Hex to provide 4-(3-chlorophenoxy)-6,7-dimethoxyquinazoline (0.05 g), white needles, m.p. 152°-153° C.

Workup

  1. temperaturewas maintained overnight at RT
  2. customThe solution is partitioned between CH2Cl2 and 5% NaOH
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash column chromatography (40% EtOAc/Hex) provided the pure compound

Sources & evidence

ORD record
ord-af2a012c8bfb4308970837eccaf1313b
Source dataset
uspto-grants-1998_02
Patent number
US05721237

Reaction notes

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