Boron tribromide → HCID 52933448, compound

HRID 1023886Notes

Reaction equation

HRID 1023886 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:15]C)[C:5]([O:13]C)=[C:6]([C:8]2[NH:12][CH:11]=[N:10][CH:9]=2)[CH:7]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:15])[C:5]([OH:13])=[C:6]([C:8]2[NH:12][CH:11]=[N:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67206667HCID 67206667, compound

Product 1

HCID 52933448HCID 52933448, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(5-chloro-2,3-dimethoxyphenyl)-1H-imidazole (0.080 g, 0.335 mmol) in dichloromethane (4 mL) at −78° C. was added BBr3 (1.01 mmol) and the reaction mixture was allowed to warm to room temperature. After stirring overnight, the reaction was quenched by cautious addition of satd. NH4Cl solution (3 mL). The product was extracted with CH2Cl2 (3×10 mL), the combined organic extract was washed with water, brine and dried (MgSO4) and concentrated in vacuum to afford the crude product. The crude was passed through a short pad of silica gel to afford the final product. Yield 62%. 1H NMR: 6.82 (d, 1H, J=2.40 Hz), 6.99 (d, 1H, J=2.40 Hz), 7.34 (s, 1H), 7.75 (s, 1H)

Workup

  1. customthe reaction was quenched by cautious addition of satd
  2. extractionThe product was extracted with CH2Cl2 (3×10 mL)
  3. extractionthe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuum
  7. customto afford the crude product

Sources & evidence

ORD record
ord-26ff0f3864e7450aa0b25ca278c60315
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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