Hydrogen Bromide → HCID 66704062, compound

HRID 424788Notes

Reaction equation

HRID 424788 reaction equation
N([O-])=O.[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2N)=[CH:11][CH:10]=1)=[O:8].[BrH:24]>CS(C)=O.C(=O)([O-])[O-].[K+].[K+].O>[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[Br:24])=[CH:11][CH:10]=1)=[O:8]

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 23668193Sodium NitriteHCID 66704060HCID 66704060, compound

Product 1

HCID 66704062HCID 66704062, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of sodium nitrite (1.40 g) in dimethyl sulfoxide (50 mL) is added 2′-amino-4′-methoxy-biphenyl-4-carboxylic acid methyl ester (2.61 g). After 5 minutes, the reaction mixture is treated with a solution of 4.7 mL hydrobromic acid (48%) in 50 mL dimethyl sulfoxide. The reaction is allowed to stir at room temperature for 2 h. The reaction mixture is diluted with a solution of 20.0 g potassium carbonate dissolved in 400 mL water. The product is extracted five times with methylene chloride. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is chromatographed eluting with hexanes/ethyl acetate (99:1 to 86:14) to give 2′-bromo-4′-methoxy-biphenyl-4-carboxylic acid methyl ester (1.00 g, 31%) as a white solid.

Workup

  1. extractionThe product is extracted five times with methylene chloride
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed
  6. washeluting with hexanes/ethyl acetate (99:1 to 86:14)

Sources & evidence

ORD record
ord-b18ce641af084999befb95e1084cf6bf
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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