Potassium Hydroxide → 2-Bromo-5-phenylthiophene-3-carboxylic acid

HRID 1914541Notes

Reaction equation

HRID 1914541 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:10][C:9]=1[Br:19])=[O:7])C>O>[Br:19][C:9]1[S:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:12][C:8]=1[C:6]([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 581102722-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester

Product 1

HCID 581103102-Bromo-5-phenylthiophene-3-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (0.65 g, 11.6 mmol) in water (2 mL) was added to a solution of 2-bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester (3.9 mmol) in IMS (6 mL). The reaction was stirred for 1 hour and then partitioned between diethyl ether and water. The aqueous layer was acidified to pH 7 with 1 N hydrochloric acid and further extracted with diethyl ether. The organic solution was dried over magnesium sulfate, filtered and the solvent evaporated to give the title compound (0.96 g, 87%). LCMS m/z 281.97 [M−H]− R.T.=3.64 min. (Analytical Method 5).

Workup

  1. custompartitioned between diethyl ether and water
  2. extractionfurther extracted with diethyl ether
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-c662300dae1e4066917c421fb4d88319
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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