Boron tribromide → HCID 22285674, compound

HRID 1168100Notes

Reaction equation

HRID 1168100 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21]O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)[Br:24]>C(Cl)Cl>[Br:24][CH2:21][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=2)=[C:6]([Cl:20])[CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11131640HCID 11131640, compound

Product 1

HCID 22285674HCID 22285674, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of Step A (75 mg, 0.22 mmol) in dry methylene chloride (2 ml) at room temperature under nitrogen was added boron tribromide (1M in methylene chloride, 0.44 ml, 0.44 mmol). The reaction mixture was stirred at room temperature for about one hour, quenched with water (5 ml) and extracted with methylene chloride (3×5 ml). The combined organic exrtracts were dried, filtered, and concentrated. The crude product was purified by preparative TLC (methylene chloride) to afford the title compound (59 mg) as an oil. MS (APCl−) Calc: 388.0, found: 386.9 (M−1).

Workup

  1. customquenched with water (5 ml)
  2. extractionextracted with methylene chloride (3×5 ml)
  3. customThe combined organic exrtracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC (methylene chloride)

Sources & evidence

ORD record
ord-80fbc149f957494ab5be4adcf7a82501
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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