Boron tribromide → HCID 135982272, compound

HRID 2042537Notes

Reaction equation

HRID 2042537 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][S:13][C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[N:5]1)([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:7]3[S:13][CH:12]=[CH:11][C:8]=3[C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59651915HCID 59651915, compound

Product 1

HCID 135982272HCID 135982272, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step 2 (1.0 g, 3.3 mmol) in 25 mL of CH2Cl2 was cooled to 0° C. and BBr3 (1M in DCM, 16.7 mL) was added dropwise. The ice-bath was removed and the reaction was stirred at rt for 1 h. The reaction mixture was then poured into 50 mL of ice cold saturated NH4Cl solution with stirring. The resulting solid was collected, washed with water (3×15 mL), and Et2O (2×15 mL) to give the product of step 3 (868 mg, 92%): Mp 256-257° C.; MS m/z 287 (M+H).

Workup

  1. customThe ice-bath was removed
  2. additionThe reaction mixture was then poured into 50 mL of ice cold saturated NH4Cl solution
  3. stirringwith stirring
  4. customThe resulting solid was collected
  5. washwashed with water (3×15 mL), and Et2O (2×15 mL)

Sources & evidence

ORD record
ord-c5d9fa59c34a4a3688ab78992d207e10
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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