Tributyltin Chloride → HCID 20090646, compound

HRID 703511Notes

Reaction equation

HRID 703511 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Mg].[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>O1CCCC1>[CH3:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 775951-Bromo-4-tert-butylbenzene2×HCID 5462224Magnesium

Product 1

HCID 20090646HCID 20090646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1-Bromo-4-(1,1-dimethylethyl)benzene (10.656 g) in dry tetrahydrofuran (40 ml) was added dropwise with stirring to magnesium metal (1.264 g) in dry tetrahydrofuran (10 ml). After the reaction had been initiated by warming the 1-bromo-4-(1,1-dimethylethyl)benzene was added dropwise at such a rate to maintain boiling of the solvent. After the addition the mixture was heated under reflux for 1 hour then cooled to room temperature and tri-n-butyltin chloride (14.12 ml) in dry tetrahydrofuran (20 ml) was added dropwise. The mixture was heated under reflux for 1 hour poured into ice water (300 ml), extracted with diethyl ether (2×100 ml), washed with sodium hydrogen carbonate (50 ml), dried (MgSO4) and the solvent removed in vacuo to give a yellow liquid which was poured on to flash silica gel (25 g) on a sinter. The product was washed through with hexane and the hexane was removed in vacuo to give a colourless liquid which was used directly in the next reaction.

Workup

  1. additionwas added dropwise at such a rate
  2. temperatureto maintain boiling of the solvent
  3. additionAfter the addition the mixture
  4. temperaturewas heated
  5. temperatureunder reflux for 1 hour
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 1 hour
  8. extractionextracted with diethyl ether (2×100 ml)
  9. washwashed with sodium hydrogen carbonate (50 ml)
  10. dry with materialdried (MgSO4)
  11. customthe solvent removed in vacuo
  12. customto give a yellow liquid which
  13. additionwas poured on to flash silica gel (25 g) on a sinter
  14. washThe product was washed through with hexane
  15. customthe hexane was removed in vacuo
  16. customto give a colourless liquid which
  17. customwas used directly in the next reaction

Sources & evidence

ORD record
ord-7ef870d33a7745c8975c13f06c345f61
Source dataset
uspto-grants-1991_01
Patent number
US04983619

Reaction notes

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