Boron tribromide → HCID 69309263, compound

HRID 1880587Notes

Reaction equation

HRID 1880587 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][CH:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][CH:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69311720HCID 69311720, compound

Product 1

HCID 69309263HCID 69309263, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (1.0M DCM, 0.32 mL) was added dropwise to a DCM (2 mL) solution containing the intermediate from Step C (71 mg, 0.24 mmol). The solution was stirred at room temperature until no starting material remained by HPLC analysis. The reaction was quenched with MeOH (1 mL) and AcOH (1 mL). The solution was then concentrated and the residue partitioned between aqueous 1N HCl and ethyl acetate. The organic phase was washed with water and brine and dried over MgSO4. The filtered solution was concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. LCMS1 3.51 min (M-31)=251

Workup

  1. customThe reaction was quenched with MeOH (1 mL) and AcOH (1 mL)
  2. concentrationThe solution was then concentrated
  3. customthe residue partitioned between aqueous 1N HCl and ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationThe filtered solution was concentrated
  7. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d4b7f0d61174efa8f7780051e98b1eb
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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