Boron tribromide → HCID 178474486, compound

HRID 235961Notes

Reaction equation

HRID 235961 reaction equation
B(Br)(Br)Br.[C:5]([NH:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH3:22])(=[O:7])[CH3:6]>C(Cl)Cl>[C:5]([NH:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH3:22])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178488951HCID 178488951, compound

Product 1

HCID 178474486HCID 178474486, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methylene chloride, 125 ml was stirred and cooled to -78° C. in an acetone-dry ice bath. Boron tribromide (7.5 ml, 0.079 mole) was added, followed by 42 (6.15 g, 0.025 mole). After a 10 minutes period at -78° C., the bath was removed and the mixture was stirred at ambient temperature under a CaCl2 drying tube for 18 hours. The mixture was quenched in ice and water (500 ml) and the resulting mixture was neutralized with saturated NaHCO3 solution to pH 7. The aqueous layer was separated and evaporated to dryness in vacuo. The residue was triturated with boiling IPA and filtered hot. Evaporation of the filtrate to dryness under reduced pressure left an oil that was chromatographed on silica gel. The product was eluted with 80CHCl3 --20CH3OH saturated with concentrated NH4OH and then triturated with CH3CN to yield 2.4 g (41%) of 43; m.p. 277°-279° C.

Workup

  1. customthe bath was removed
  2. customThe mixture was quenched in ice
  3. customThe aqueous layer was separated
  4. customevaporated to dryness in vacuo
  5. customThe residue was triturated with boiling IPA
  6. filtrationfiltered hot
  7. customEvaporation of the filtrate to dryness under reduced pressure
  8. waitleft an oil that
  9. customwas chromatographed on silica gel
  10. washThe product was eluted with 80CHCl3
  11. custom20CH3OH saturated with concentrated NH4OH and then triturated with CH3CN

Sources & evidence

ORD record
ord-f0ae9c00c1f3449d90c5c53be787da23
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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