Boron tribromide → HCID 91416132, compound

HRID 857371Notes

Reaction equation

HRID 857371 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([CH:19]([CH3:21])[CH3:20])=[CH:13][C:14]([O:17]C)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([CH:19]([CH3:20])[CH3:21])=[CH:13][C:14]([OH:17])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 91430685HCID 91430685, compound

Product 1

HCID 91416132HCID 91416132, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Step 2 (170 mg, 0.56 mmol) in CH2Cl2 (5 mL) at 0° C. was added slowly BBr3 1.0 M in dichloromethane (2.8 mL, 2.8 mmol) dropwise. The reaction mixture was warmed to r.t. for 30 minutes then cooled to −78° C., quenched with MeOH (5 mL), extracted with CH2Cl2, and washed with a saturated aqueous solution of NaHCO3. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (130 mg).

Workup

  1. temperaturethen cooled to −78° C.
  2. customquenched with MeOH (5 mL)
  3. extractionextracted with CH2Cl2
  4. washwashed with a saturated aqueous solution of NaHCO3
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e4d73b8f03f4546b23f1ab2e119a794
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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