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

HRID 557622Notes

Reaction equation

HRID 557622 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:23])C)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].BrBr.[OH-].[Na+].Cl.S(S([O-])=O)([O-])(=O)=[O:30].[Na+].[Na+]>O1CCOCC1.O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:30])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 656671Sodium PyrosulfiteHCID 66660270Ethyl 1-(4'-acetyl-[1,1'-biphenyl]-4-yl)cyclopropanecarboxylate

Product 1

HCID 666606254'-(1-(Ethoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To 1-(4′-acetylbiphenyl-4-yl)cyclopropanecarboxylic acid ethyl ester (10.1 g, 33 mmol) in dioxane (200 mL) at ˜10° C. was added a solution of bromine (26.4 g, 165 mmol), sodium hydroxide (22.4 g, 561 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 4′-(1-(ethoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid.

Workup

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

Sources & evidence

ORD record
ord-9ffa609182d44ee99dd38d60f1dd8c74
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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