Boron tribromide → HCID 14392485, compound

HRID 1382142Notes

Reaction equation

HRID 1382142 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9]C)=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH:17]([F:19])[F:18])[C:13]([CH3:20])=[N:12]1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH:17]([F:19])[F:18])[C:13]([CH3:20])=[N:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21274220HCID 21274220, compound

Product 1

HCID 14392485HCID 14392485, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 16.0 g (0.053 mole) of 1-(2-chloro-4-methyl-5-methoxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 100 mL of methylene chloride at 10° C. was added dropwise 39.6 g (0.16 mole) of boron tribromide. The resultant mixture was stirred at room temperature for two days. This mixture was washed with 100 mL of water. The organic layer was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to leave an oil. This oil was stirred in petroleum ether:diethyl ether (90:10) forming a solid. The solid was collected by filtration to yield 10.5 g of 1-(2-chloro-4-methyl-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one (mp 154°-156° C.).

Workup

  1. washThis mixture was washed with 100 mL of water
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto leave an oil
  6. customforming a solid
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-88f8028028b842c6b5abf580ba0a0c6f
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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