Boron tribromide → HCID 66704224, compound

HRID 424789Notes

Reaction equation

HRID 424789 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66704062HCID 66704062, compound

Product 1

HCID 66704224HCID 66704224, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2′-bromo-4′-methoxy-biphenyl-4-carboxylic acid methyl ester (0.200 g) in methylene chloride (5 mL) is added boron tribromide (0.176 mL). The reaction mixture is maintained at 0° C. for 2 h. The reaction mixture is slowly quenched with 50 mL methanol, diluted with 150 mL 2N hydrochloric acid, and extracted three times with methylene chloride. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.180 g, 94%).

Workup

  1. customThe reaction mixture is slowly quenched with 50 mL methanol
  2. additiondiluted with 150 mL 2N hydrochloric acid
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d7b5fd947724843befe77c91ed76e48
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

Loading…