Hydrochloric Acid → 1-(4-Bromo-2-methoxyphenyl)cyclobutanecarboxylic acid

HRID 338507Notes

Reaction equation

HRID 338507 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1.[OH2:16].Cl.[OH-:18].[K+]>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:18])=[O:16])[CH2:11][CH2:10][CH2:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 866988391-(4-Bromo-2-methoxyphenyl)cyclobutanecarbonitrile

Product 1

HCID 866988401-(4-Bromo-2-methoxyphenyl)cyclobutanecarboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarbonitrile (370 mg, 1.04 mmol) in aqueous KOH (80%, 5 mL) and ethylene glycol (5 mL) was heated at 100° C. and stirred for 16 hours. The mixture was added water (20 ml) and acidified by concentrated HCl to pH=1 and extracted with dichloromethane. The combined organic layers was dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (327 mg, 82%) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 7.19 (d, 1H), 7.13 (s, 1H), 7.12 (d, 1H), 3.72 (s, 3H), 2.59 (m, 2H), 2.30 (q, 2H), 2.05 (m, 1H), 1.78 (m, 1H)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f457bca0c10347b999bd81d6abe4da3f
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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