3-Bromothiophene → Di(3-thienyl)methanol

HRID 742466Notes

Reaction equation

HRID 742466 reaction equation
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1.[S:12]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13]1.[Cl-].[NH4+]>C1COCC1>[S:9]1[CH:10]=[CH:11][C:7]([CH:17]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)[OH:18])=[CH:8]1

Participants

6

Reactant 4

HCID 133833-BromothiopheneHCID 25517Ammonium ChlorideHCID 681353-ThiophenecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 288490Di(3-thienyl)methanolYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 mL of THF cooled to -78° C. under nitrogen was added 2.5M n-butyllithium (36 mL), and 14.67 g (0.09 mol) of 3-bromothiophene was added and the resulting mixture was stirred for 30 min. To the above mixture was added 3-thiophenecarboxaldehyde (10 g, 0.089 mol) in 10 mL of THF and the mixture was stirred, allowing it to reach room temperature. Saturated ammonium chloride solution was added to the reaction mixture, the aqueous layer was extracted with ether, and the combined organic layer was concentrated in vacuo to yield 17.26 g (98.9%) of 1,1-di(3-thienyl)methanol, as an oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. customto reach room temperature
  4. extractionthe aqueous layer was extracted with ether
  5. concentrationthe combined organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-063a47eefc414105b384aabb9d3e15fb
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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