HCID 15541117, compound → HCID 14116663, compound

HRID 381817Notes

Reaction equation

HRID 381817 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15541117HCID 15541117, compound

Product 1

HCID 14116663HCID 14116663, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester (2.636 g, 0.00759 mol) in 6 M HCl was refluxed for 214 hours and cooled to room temperature. The solids were filtered and washed with 1 M HCl. The filter cake was partitioned between ethyl acetate and 1 M sodium hydroxide. The aqueous layer was washed twice with ethyl acetate and filtered to remove particulates. The filtrate was rotary evaporated to remove residual ethyl acetate. The solution was stirred and acidified to pH 2 with concentrated HCl solution. The resulting precipitate was filtered, washed with water, and dried with house vacuum (air bleed) give 1.97 g of 4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid as a white solid; mp 198-200° C.

Workup

  1. temperaturewas refluxed for 214 hours
  2. filtrationThe solids were filtered
  3. washwashed with 1 M HCl
  4. customThe filter cake was partitioned between ethyl acetate and 1 M sodium hydroxide
  5. washThe aqueous layer was washed twice with ethyl acetate
  6. filtrationfiltered
  7. customto remove particulates
  8. customThe filtrate was rotary evaporated
  9. customto remove residual ethyl acetate
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water
  12. customdried with house vacuum (air bleed)

Sources & evidence

ORD record
ord-2ad9bc6407804a40962ccc784eb89739
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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