Sodium Hydroxide → rac-(1R,2R)-2-(4-bromophenyl)cyclopropane-1-carboxylic acid

HRID 709404Notes

Reaction equation

HRID 709404 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([O:15]CC)=[O:14])=[CH:6][CH:5]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate2×

Product 1

HCID 12586658rac-(1R,2R)-2-(4-bromophenyl)cyclopropane-1-carboxylic acidYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH 4N (20 mL) was added to a solution of (trans)-ethyl 2-(4-bromophenyl)cyclopropanecarboxylate (Intermediate I, 4 g, 0.0149 mol), in Methanol (40 mL) and stirred at rt for 2 h. After completion of reaction, checked by TLC, the solvent was evaporated and the residue was diluted with water (50 mL), acidified with HCl 4 N solution, the solid formed was filtered and dried to get (trans)-2-(4-bromophenyl)cyclopropanecarboxylic acid (2.59 g, 72%), as a white solid.

Workup

  1. customAfter completion of reaction
  2. customthe solvent was evaporated
  3. additionthe residue was diluted with water (50 mL)
  4. customthe solid formed
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-2ace9d22471c44bd9ab9a7fbea20b5dd
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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