Boron tribromide → HCID 59283054, compound

HRID 1965835Notes

Reaction equation

HRID 1965835 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6](/[CH:7]=[CH:8]/[C:9]2[S:13][C:12]([C:14]3[CH:22]=[CH:21][C:17]([N:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=3)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:20][N:18]([CH3:19])[C:17]1[CH:16]=[CH:15][C:14]([C:12]2[S:13][C:9](/[CH:8]=[CH:7]/[C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:24][CH:23]=3)=[CH:10][N:11]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59283045HCID 59283045, compound

Product 1

HCID 59283054HCID 59283054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 10 mL round bottomed flask equipped with a magnetic stir bar containing DCM (5 mL) was placed 264 (0.1 g, 0.3 mmol), the reaction mixture was cooled to 0° C., BBr3 (0.8 mL of 1M in DCM) was added drop wise and was stirred at RT for 3 hrs. The reaction was neutralized with sat. NaHCO3, extracted into DCM (3×15 mL). The combined organic extracts were washed with water (15 mL), brine (15 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified over silica gel using THF:Hexanes (3:2) as an eluent to afford UG-4-69 (0.01 g, 10%) as a white solid.

Workup

  1. customTo a 10 mL round bottomed flask equipped with a magnetic stir bar
  2. extractionextracted into DCM (3×15 mL)
  3. washThe combined organic extracts were washed with water (15 mL), brine (15 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified over silica gel
  7. customto afford UG-4-69 (0.01 g, 10%) as a white solid

Sources & evidence

ORD record
ord-89e1b44c740245beac8e9f6b8193fc1a
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

Loading…