Benzyl Bromide → HCID 71258628, compound

HRID 1770362Notes

Reaction equation

HRID 1770362 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:18]([OH:26])([CH3:25])[CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1.[Cl-].[Na+].O>[CH2:27]([O:26][C:18]([C:5]1[CH:6]=[CH:7][C:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:9][C:4]=1[Cl:3])([CH3:25])[CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 44126848HCID 44126848, compound

Product 1

HCID 71258628HCID 71258628, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (0.04 g) was added to a solution of 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (0.5 g) in THF (15 mL). After 30 min benzylbromide (0.27 g) was added and the mixture was stirred for 18 h at reflux. Brine was added and the mixture was extracted with dichloro methane (3×). The combined organic phases were dried, filtered through a silica plug and evaporated. The crude product was purified by column chromatography to yield 0.43 g of the desired compound.

Workup

  1. temperatureat reflux
  2. extractionthe mixture was extracted with dichloro methane (3×)
  3. customThe combined organic phases were dried
  4. filtrationfiltered through a silica plug
  5. customevaporated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-81819ec5bb3a40008e2b5919bcd1f621
Source dataset
uspto-grants-2016_02
Patent number
US09247746B2

Reaction notes

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