tert-Butyl methyl ether → HCID 117600279, compound

HRID 1496989Notes

Reaction equation

HRID 1496989 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[N:5][N:6]=1.[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[CH:11]=[O:12].[NH4+].[Cl-].CC(OC)(C)C>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:11]([C:4]2[O:3][C:2]([CH3:1])=[N:6][N:5]=2)[OH:12])[CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 5584472-Methyl-1,3,4-oxadiazoleHCID 161154383-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 117600279HCID 117600279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.79 g (33.2 mmol) of 2-methyl-1,3,4-oxadiazole are dissolved in 45 ml THF at −5° C., 33.2 mmol (25.54 ml) of isopropyl magnesium chloride-lithium chloride complex are added during 20 minutes while the temperature is kept <0° C. The mixture is kept at 0° C. for 30 minutes, then 0.8 Eq (6.7 g) of 3-Bromo-5-trifluoromethyl-benzaldehyde are added and the resulting mixture is allowed to reach RT and stirred for additional 60 minutes. The reaction is then stopped by the addition of 10 ml saturated NH4Cl solution. 50 ml MTBE are added, the organic phase is separated, washed with brine and dried over MgSO4. The solvent is removed in vacuo and the crude material (9 g) is used without further purification in the next step:

Workup

  1. addition33.2 mmol (25.54 ml) of isopropyl magnesium chloride-lithium chloride complex are added during 20 minutes while the temperature
  2. customis kept <0° C
  3. customto reach RT
  4. customthe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed in vacuo
  8. customthe crude material (9 g) is used without further purification in the next step

Sources & evidence

ORD record
ord-c739b3feb479468aab6b76fc13d2cde0
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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