Hydrochloric Acid → 4'-(1-(Isopropoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid

HRID 2391052Notes

Reaction equation

HRID 2391052 reaction equation
[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[O:24])C)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].BrBr.[OH-].[Na+].Cl.S(S([O-])=O)([O-])(=O)=[O:31].[Na+].[Na+]>O1CCOCC1.O>[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])=[O:24])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 656671Sodium PyrosulfiteHCID 666602881-(4'-Acetylbiphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester

Product 1

HCID 666604224'-(1-(Isopropoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To 1-(4′-acetylbiphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester (11.6 g, 36 mmol) in dioxane (200 mL) at ˜10° C. was added a solution of bromine (28.8 g, 180 mmol), sodium hydroxide (24.5 g, 612 mmol) in water (150 mL). The solution was stirred at room temperature for 30 minutes poured into water (500 mL) and acidified with dilute hydrochloric acid. Sodium metabisulfite was added until the brown bromine color dissipated. The product was filtered and dried in a vacuum over overnight at 40° C. to yield 10 g of the title compound.

Workup

  1. filtrationThe product was filtered
  2. customdried in a vacuum over overnight at 40° C.

Sources & evidence

ORD record
ord-08876ff5ff20484aa14f108a5af395de
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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