Boron tribromide → HCID 10476241, compound

HRID 2105271Notes

Reaction equation

HRID 2105271 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=1[S:11]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:16]=1[CH3:29])(=[O:13])=[O:12].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=1[S:11]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:16]=1[CH3:29])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86594269HCID 86594269, compound

Product 1

HCID 10476241HCID 10476241, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atomersphere, 32 (88 mg, 0.21 mmol) was dissolved in dichloromethane (6 mL) followed by the addition of BBr3 (0.2 mL, 2.1 mmol). The reaction was stirred overnight at room temperature and then quenched with ice. The mixture was partitioned between EtOAc and water and the organic layer was separated, washed with brine, and dried over Na2SO4. The solids were filtered off and the filtrate was concentrated in a rotavap to give 70 mg of the title compound as a brownish solid ESI [M+H+]=402.24.

Workup

  1. customquenched with ice
  2. customThe mixture was partitioned between EtOAc and water
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe solids were filtered off
  7. concentrationthe filtrate was concentrated in a rotavap

Sources & evidence

ORD record
ord-422fbfedad00411b87bd269f16f4db53
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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