Acetone → HCID 86691459, compound

HRID 1618860Notes

Reaction equation

HRID 1618860 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH:12]([CH3:14])[N:11]([CH3:15])[C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1.C(=O)=O.CC(C)=O.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH:12]([CH3:14])[N:11]([CH3:15])[C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 25134Boron tribromideHCID 86691457HCID 86691457, compound

Product 1

HCID 86691459HCID 86691459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

Product of Step 5 (5 g) was dissolved in dichloromethane (250 mL) and stirred at −60° C. under argon purging using dry ice and acetone. After 30 min at −60° C. and under argon purging, 1M boron tribromide in dichloromethane (45 mL) was added in drop wise manner. The reaction mixture was stirred for 3 hr at −60° C. under argon purging. Then, the reaction mixture was allowed to warm to 25° C. and stirred under argon for 2 hr at 25° C. The reaction was quenched with slow addition of methanol (50 mL) at 4° C. The reaction mixture was concentrated under vacuum and poured in cold 1N HCl (300 mL). The white precipitate was extracted with dichloromethane (500 mL). The organic layer was dried on anhydrous magnesium sulfate, was filtered and was concentrated under vacuum. The crude product was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 3 hr at −60° C. under argon purging
  2. temperatureto warm to 25° C.
  3. stirringstirred under argon for 2 hr at 25° C
  4. customThe reaction was quenched with slow addition of methanol (50 mL) at 4° C
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. additionpoured in cold 1N HCl (300 mL)
  7. extractionThe white precipitate was extracted with dichloromethane (500 mL)
  8. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  9. filtrationwas filtered
  10. concentrationwas concentrated under vacuum
  11. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-16b87b0a0cd14172ae5a6c9f188fc68a
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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