Hydrochloric Acid → 3-([1,1'-Biphenyl]-4-YL)propiolic acid

HRID 76142Notes

Reaction equation

HRID 76142 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([CH:7](Br)[CH:8](Br)[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].Cl>CC(O)(C)C>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxide2×HCID 72698664HCID 72698664, compound

Product 1

HCID 654541843-([1,1'-Biphenyl]-4-YL)propiolic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

5.00 g (13.0 mmol) 3-biphenyl-4-yl-2,3-dibromo-propionic acid are added to 40 mL tBuOH. Over a period of 25 min 5.80 g (52.1 mmol) KOtBu are added in several portions while keeping the temperature below 35° C. Then the reaction mixture is stirred at 40° C. for 2 h. Again 1.40 g (12.5 mmol) potassium tert-butoxide are added and the mixture is stirred for additional 2 h at 40° C. Then the mixture is allowed to cool to r.t. and poured onto icewater/concentrated HCl. The precipitate is filtered and partitioned between EtOAc and water. The organic layer is washed with water, dried and the solvent is removed in vacuo. The crude product is triturated with PE, filtered and dried at 80° C. in vacuo.

Workup

  1. customthe temperature below 35° C
  2. stirringthe mixture is stirred for additional 2 h at 40° C
  3. temperatureto cool to r.t.
  4. filtrationThe precipitate is filtered
  5. custompartitioned between EtOAc and water
  6. washThe organic layer is washed with water
  7. customdried
  8. customthe solvent is removed in vacuo
  9. customThe crude product is triturated with PE
  10. filtrationfiltered
  11. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-48d3980eae324a4d837ae7c1ffaeb421
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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