Water → HCID 58160698, compound

HRID 1943519Notes

Reaction equation

HRID 1943519 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[C:12]([F:21])[CH:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Li]CCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:37])(=O)=O)=CC=1.O>C1COCC1>[F:37][C:18]1[S:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=3)=[CH:11][C:12]=2[F:21])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 588007N-FluorobenzenesulfonimideHCID 58160694HCID 58160694, compoundHCID 178418339Butyllithium

Product 1

HCID 58160698HCID 58160698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4.0 g (13.5 mmol) of 2-(4′-propyl-3-fluorobiphenyl-4-yl)thiophene (“PGT-3-H”) are initially introduced at −20° C. in THF, and 9.3 ml (14.8 mmol) of n-BuLi (15% solution in hexane) are added dropwise. The mixture is warmed to 0° C. and stirred at this temperature for 30 min. The batch is cooled to −78° C., and a solution of 5.11 g (16.2 mmol) of N-fluorobenzenesulfonimide (NFSI) in THF is metered in. After 30 min at −78° C., the batch is warmed to room temperature. Water is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and sat. sodium chloride solution and dried using sodium sulfate. The solution is evaporated to dryness, and the residue is purified by chromatography (SiO2, n-pentane). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-fluoro-5-(3-fluoro-4′-propylbiphenyl-4-yl)thiophene (“PGT-3-F”) as a colourless solid having an m.p. of 64° C.

Workup

  1. temperatureThe batch is cooled to −78° C.
  2. waitAfter 30 min at −78° C.
  3. temperaturethe batch is warmed to room temperature
  4. extractionthe mixture is extracted a number of times with MTBE
  5. washThe combined organic phases are washed with water and sat. sodium chloride solution
  6. customdried
  7. customThe solution is evaporated to dryness
  8. customthe residue is purified by chromatography (SiO2, n-pentane)
  9. customThe further purification
  10. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-629510c7f5874872be585cca13357eba
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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