Boron tribromide → HCID 22285674, compound

HRID 1062481Notes

Reaction equation

HRID 1062481 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 extracts 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 (APCI−) 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 extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC (methylene chloride)

Sources & evidence

ORD record
ord-968f358479834daa9047e1fef4d8a799
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

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