Sodium Hydroxide → trans-2-(4-Bromobenzoyl)cyclopropanecarboxylic acid

HRID 2427324Notes

Reaction equation

[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:7])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate (10.34 g, 36.52 mmol) was dissolved in MeOH (100 mL), and then 15 mL 50% aqueous NaOH solution was added. The reaction mixture was stirred at 40° C. for 3 days. Solvent was removed by rotary evaporation and the residue was dissolved in water. Concentrated HCl was added to adjust the acidity to pH 1. The precipitate that formed was collected by filtration and dried in a vacuum oven overnight to give trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.43 g, 95%). LC-MS ret. time 2.51, m/z 270 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.68 (m, 2H), 2.38 (m, 1H), 3.22 (m, 1H), 7.67 (m, 2H), 7.90 (m, 2H).

Workup

customSolvent was removed by rotary evaporation
dissolutionthe residue was dissolved in water
additionConcentrated HCl was added
customThe precipitate that formed
filtrationwas collected by filtration
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-5bcc7f85e93744cdbe020ff8b237c42b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968576B2

Reaction notes

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