Boron tribromide → HCID 14349357, compound

HRID 846509Notes

Reaction equation

HRID 846509 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9]C)=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH3:19])[N:13]=[N:12]1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH3:19])[N:13]=[N:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19882797HCID 19882797, compound2×

Product 1

HCID 14349357HCID 14349357, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a dry nitrogen atmosphere a stirred solution of 0.18 G (0.00067 mole) of 1-(2,4-difluoro-5-methoxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one (compound 10) in 5 mL of methylene chloride was cooled to -40° C. To this cold solution was added dropwise a solution of 0.5 g (0.002 mole) of boron tribromide in 5 mL of methylene chloride. After complete addition, the mixture was allowed to warm to room temperature and was stirred for approximately 70 hours. The mixture was poured into ice water and the two phases separated. The aqueous phase was extracted with methylene chloride. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to leave 0.14 g of 1-(2,4-difluoro-5-hydroxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 65°-67° C.

Workup

  1. additionAfter complete addition
  2. customthe two phases separated
  3. extractionThe aqueous phase was extracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-907a5693e31a4063b84e917fe4adf9b1
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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