Boron tribromide → HCID 56946411, compound

HRID 2042550Notes

Reaction equation

HRID 2042550 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([CH3:15])=[N:13][N:12]([CH3:16])[C:11](=[O:17])[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([CH3:15])=[N:13][N:12]([CH3:16])[C:11](=[O:17])[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 56946410HCID 56946410, compound

Product 1

HCID 56946411HCID 56946411, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step 1 (3.2 g, 14 mmol) in CH2Cl2 (40 mL) was cooled to 0° C. and BBr3 (6.6 mL, 5.0 eq.) was added dropwise. The ice-bath was removed and the reaction was stirred at rt for 1 h, after which the reaction mixture was poured into 50 mL of ice cold saturated NH4Cl solution with stirring. The resulting solid was filtered, and washed with water (3×15 mL) then Et2O (2×15 mL) to give the product of step 2 (0.66 g, 22%): MS m/z 217 (M+H).

Workup

  1. customThe ice-bath was removed
  2. additionafter which the reaction mixture was poured into 50 mL of ice cold saturated NH4Cl solution
  3. stirringwith stirring
  4. filtrationThe resulting solid was filtered
  5. washwashed with water (3×15 mL)

Sources & evidence

ORD record
ord-e5615837800942998c2e5a03820cccca
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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