Water → 5-(2-Hydroxyphenyl)-thiophene-2-carboxylic acid

HRID 1359639Notes

Reaction equation

HRID 1359639 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[OH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 10340Sodium CarbonateHCID 3491155-Bromothiophene-2-carboxylic acid

Product 1

HCID 223508435-(2-Hydroxyphenyl)-thiophene-2-carboxylic acidYield 84.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(O) (133 mg, 0.12 mmol) is added to a solution of 5-bromothiophene-2-carboxylic acid (850 mg, 4.1 mmol) in degassed THF (10 mL). The resulting solution is stirred for 5 minutes and then 2,4,4,5,5-tetramethyl)-1,3,2-dioxaborolan-2-yl) phenol (1 g, 4.6 mmol) is added followed by aqueous Na2CO3 (2M, 6.9 mL). The mixture is heated at reflux overnight. The reaction mixture is allowed to cool, poured into water (50 mL), and washed with ether (3×50 mL). The aqueous layer is acidified with concentrated HCl to pH<2. The resulting precipitate is collected by filtration, washed with water and dried in vacuo to yield the desired product (761 mg, 83%). MS for C11H7O3S (ESI) (M−H)+ m/z 219.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. washwashed with ether (3×50 mL)
  5. filtrationThe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-771a0968388241e3a2436540561277de
Source dataset
uspto-grants-2003_07
Patent number
US06599916B2

Reaction notes

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