Tetrahydrofuran → 3-Bromo-4-hexylthiophene

HRID 83958Notes

Reaction equation

HRID 83958 reaction equation
Br[C:2]1[S:3][C:4](Br)=[C:5]([Br:13])[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1COCC1.C([Li])CCC>O>[Br:13][C:5]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:2][S:3][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 161034832,4,5-Tribromo-3-hexylthiopheneHCID 178418339Butyllithium

Product 1

HCID 161034523-Bromo-4-hexylthiopheneYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 51 (70 g, 0.173 mol) is mixed with dry THF (400 mL). To this mixture, n-butyllithium (138 mL, 2.5M in hexane, 0.345 mol) is added dropwise at −78° C. under argon. The resulting mixture is stirred for 10 minutes, then water (30 mL) is added to quench the reaction. The THF is evaporated and the organic is extracted with ethyl acetate (2×100 mL). The combined organic layers are washed with brine (2×100 mL), water (70 mL) and dried over MgSO4. After evaporation of the solvent, the resulting crude product is purified by vacuum distillation (72-74° C. at 0.17 mbar) to yield 52 (35.3 g, 82.6% yield). GC/MS: 246 g/mol (M−1). 1H NMR (CD2Cl2): δ 7.22 (s, 1H), 6.96 (s, 1H), 2.57 (t, 2H), 1.61 (m, 2H), 1.32 (m, 6H), 0.88 (t, 3H). 13C NMR: 141.92, 122.87, 120.95, 112.89, 31.88, 30.07, 29.53, 29.20, 22.88, 14.14.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe THF is evaporated
  4. extractionthe organic is extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layers are washed with brine (2×100 mL), water (70 mL)
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of the solvent
  8. distillationthe resulting crude product is purified by vacuum distillation (72-74° C. at 0.17 mbar)

Sources & evidence

ORD record
ord-df463bbafd8b4699a2ca4715c56c9a66
Source dataset
uspto-grants-2014_09
Patent number
US08846855B2

Reaction notes

Loading…