Water → 2-(4-Bromophenyl)-5-chloro-pentanoic acid

HRID 220198Notes

Reaction equation

HRID 220198 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][Cl:14])[C:9]#N)=[CH:4][CH:3]=1.[OH:15]S(O)(=O)=O.[OH2:20]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][Cl:14])[C:9]([OH:15])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 592383202-(4-Bromophenyl)-5-chloropentane nitrile

Product 1

HCID 592382802-(4-Bromophenyl)-5-chloro-pentanoic acidYield 90%

Procedure

The 2-(4-bromophenyl)-5-chloropentane nitrile (4 g, 14.7 mmol) was hydrolyzed by refluxing for 12 h with a 3:5:3 mixture of concentrated H2SO4, glacial acietic acid, and water (33 mL). The reaction mixture was cooled to room temperature, diluted with water, and extracted with CHCl3. The organic layer was washed with brine (3 times), then dried with MgSO4, the solution was evaporated to dryness under reduced pressure, giving an oil (3.8 g, 90%). MS: calc'd 290 (MH+), exp 290 (MH+). 1H NMR (400 MHz, CDCl3), 7.46-7.56 (2H), 7.10-7.20 (2H), 3.84 (1H), 3.52 (3H), 1.60-2.20 (4H).

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with brine (3 times)
  3. dry with materialdried with MgSO4
  4. customthe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-463fb7c47aeb43a89b92ee4f6a7f8cdc
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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