Boron tribromide → HCID 59283003, compound

HRID 1965836Notes

Reaction equation

HRID 1965836 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6](/[CH:7]=[CH:8]/[N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][C:10]2=[O:18])=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:7]=[CH:8]/[N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][C:10]2=[O:18])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59283055HCID 59283055, compound

Product 1

HCID 59283003HCID 59283003, compoundYield 95%

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 (4 mL) was placed 6 (0.1 g, 0.39 mmol), the reaction mixture was cooled to 0° C., BBr3 (1.0 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 EtOAc:Hexanes (1:4) as an eluent to afford 7 (0.09 g, 95%) 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

Sources & evidence

ORD record
ord-fe8c74388e774c0593722b88997eee7a
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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