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

HRID 557627Notes

Reaction equation

HRID 557627 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-b5e02b4f28314d53a065d350aa938215
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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