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

HRID 1470545Notes

Reaction equation

HRID 1470545 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 B, 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-9cb6db798966460ea548671b88823b7a
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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