Potassium Hydroxide → HCID 59138611, compound

HRID 1514075Notes

Reaction equation

HRID 1514075 reaction equation
C[O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH:5]([C:13]1[S:14][C:15]([Br:18])=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1.[OH-].[K+]>CO.CS(C)=O>[Br:18][C:15]1[S:14][C:13]([CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[C:4]([CH3:20])([CH3:19])[C:3]([OH:21])=[O:2])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59138598HCID 59138598, compound

Product 1

HCID 59138611HCID 59138611, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-(5-bromo-thiophen-2-yl)-3-(3-fluoro-phenyl)-2,2-dimethyl-propionic acid methyl ester (419 mg, 1.128 mmol) in MeOH (4 ml) and DMSO (2 ml) was added a 40% aqueous solution of potassium hydroxide (4 ml). The reaction mixture was heated at 75° C. for 6 hours. After removal of methanol, the solution was adjusted to pH 2 and was extracted with ethyl ether. The ether layer was washed, dried and evaporated to give 3-(5-bromo-thiophen-2-yl)-3-(3-fluoro-phenyl)-2,2-dimethyl-propionic acid (1a) as a white glass (346.2 mg, 86% yield). 1H NMR (400 MHz, CDCl3): δ 1.06 (s, 3H), 1.15 (s, 3H), 3.21 (s, 1H), 6.75 (d, 1H, J=3.8 Hz), 6.82 (d, 1H, J=3.8 Hz), 6.87 (td, 1H, J=8.1, 2.6 Hz), 7.02 (m, 1H), 7.10 (br d, J=8.1 Hz), 7.20 (m, 1H). HPLC Rt: 3.695 min.

Workup

  1. customAfter removal of methanol
  2. extractionwas extracted with ethyl ether
  3. washThe ether layer was washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-1036877008654eab9b4fdc167adebbf8
Source dataset
uspto-grants-2012_07
Patent number
US08222247B2

Reaction notes

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