Chlorotrimethylsilane → HCID 21848596, compound

HRID 399311Notes

Reaction equation

HRID 399311 reaction equation
[Br:1][C:2]1[C:6]([Br:7])=[C:5]([CH:8]([OH:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[NH:4][C:3]=1[CH:20]([OH:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24].[H-].[Na+].[H][H].[CH3:36][Si:37](Cl)([CH3:39])[CH3:38]>C1COCC1>[Br:1][C:2]1[C:6]([Br:7])=[C:5]([CH:8]([O:19][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:9]([F:17])([F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[NH:4][C:3]=1[CH:20]([O:31][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[C:23]([F:26])([F:24])[F:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 21848597HCID 21848597, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21848596HCID 21848596, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dibromo-2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (1 mmol, 0.62 g) was dissolved in 25 ml of dry THF and transferred to a cooled (0° C.) suspension of sodium hydride (2.0 mmol, 0.048 g) in 100 mL of THF. When hydrogen evolution ceased (after 2 hours) trimethylsilyl chloride (2 mmol, 0.218 g) was added by syringe. The mixture was stirred at room temperature overnight before the solvent was removed in vacuo. The remaining residue was partitioned between 10% sodium bicarbonate solution and ether and the organic layer was dried over magnesium sulfate, filtered and evaporated to leave a brown oil. The product was purified by chromatography on silica gel using hexane as eluant. The product was the first material off the column (rf =0.5) The fractions containing this spot were evaporated to leave a colorless oil which solidified upon cooling under vacuum to leave 3,4-dibromo-2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-trimethylsilyloxy-butyl)pyrrole as white needles. (380 mg, 50% yield) 1H NMR (360 MHz, CDCl3) 8.84 (broad s, 1 H); 5.30 (dd, 2 H, J1=19.5, J2=1.0); 0.06 (s, 18 H).

Workup

  1. temperaturea cooled
  2. additionwas added by syringe
  3. customwas removed in vacuo
  4. customThe remaining residue was partitioned between 10% sodium bicarbonate solution and ether
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil
  9. customThe product was purified by chromatography on silica gel
  10. additioncontaining this spot
  11. customwere evaporated
  12. customto leave a colorless oil which
  13. temperatureupon cooling under vacuum

Sources & evidence

ORD record
ord-ffc082e835ff4333b4930e31c0dd60d4
Source dataset
uspto-grants-1998_10
Patent number
US05817830

Reaction notes

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