Hydrochloric Acid → 2-(4-Methoxyphenyl)-5-pentylthiophene

HRID 2121296Notes

Reaction equation

HRID 2121296 reaction equation
Br[C:2]1[S:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:5][CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(COC)OC>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[S:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:5][CH:6]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 113108252-bromo-5-pentylThiophene

Product 1

HCID 234321132-(4-Methoxyphenyl)-5-pentylthiopheneYield 77.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-bromo-5-pentylthiophene (10.0 g), 4-methoxyphenyl boronic acid (7.9 g), 2M aqueous sodium carbonate solution (150 cm3), 2.3 g tetrakis(triphenylphosphine)palladium (0) and dimethoxyethane (100 cm3) was heated under reflux for 6 h. 20% Hydrochloric acid (200 cm3) was added to the cooled reaction mixture and the resultant mixture extracted with diethyl ether (5×100 cm3). The combined organic layers were washed with 20% hydrochloric acid (1×100 cm3), brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue was purified by column chromatography on silica gel using a 4:1 hexane/dichloromethane mixture as eluent and recrystallisation from ethanol to yield 8.7 g of 2-(4-methoxyphenyl)-5-pentylthiophene, K 58-60° C., I.

Workup

  1. temperatureunder reflux for 6 h
  2. extractionthe resultant mixture extracted with diethyl ether (5×100 cm3)
  3. washThe combined organic layers were washed with 20% hydrochloric acid (1×100 cm3), brine (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue was purified by column chromatography on silica gel using a 4:1 hexane/dichloromethane mixture as eluent
  8. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-4d3d35185a2948059636b77fd5a9410f
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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