Trimethylstannane → Trimethyltin 2,5-dichlorobenzenesulfinate

HRID 1706850Notes

Reaction equation

HRID 1706850 reaction equation
[CH3:1][SnH:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[S:13]([OH:15])=[O:14].[H][H]>C1(C)C(C)=CC=CC=1.C(OCC)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[S:13]([O-:15])=[O:14].[CH3:1][Sn+:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 12623TrimethylstannaneHCID 69139172,5-dichlorobenzenesulfinic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 20332839Trimethyltin 2,5-dichlorobenzenesulfinate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

A 100 ml three-necked flask, fitted with a reflux condenser and addition funnel, was flushed thoroughly with nitrogen and charged with 4.5 ml (29.4 mmoles) of a solution of trimethyltin hydride in xylene (78 volume/volume %). To this solution was added dropwise with stirring at room temperature 70 ml of a solution of 6.0 g (28.5 mmoles) of 2,5-dichlorobenzenesulfinic acid in diethyl ether. Evolution of hydrogen occurred immediately and throughout the addition which lasted one hour. The flask was cooled in ice-water, and 9.38 g of solid was collected on a filter. The solid was recrystallized from cyclohexaneligroin giving 9.28 g of trimethyltin 2,5-dichlorobenzenesulfinate, m.p. 126.3°-128.8° C. The presence of strong absorption bands at 950 and 980 cm-1, characteristic of the ##STR19## in organotin sulfinates, was observed in the infrared spectrum (KBr). The NMR spectrum showed the following characteristics: The aromatic proton ortho to the sulfinato group appeared as a multiplet centered at 765 Hz (1 proton); the remaining aromatic protons appeared as a multiplet centered at 727 Hz (2 protons); the protons of the trimethyltin group appeared as a singlet at 62 Hz flanked on either side by two satellite bands (9 protons).

Workup

  1. customA 100 ml three-necked flask, fitted with a reflux condenser and addition funnel
  2. customwas flushed thoroughly with nitrogen
  3. additionTo this solution was added dropwise
  4. custom9.38 g of solid was collected on a filter
  5. customThe solid was recrystallized from cyclohexaneligroin

Sources & evidence

ORD record
ord-b31fa2e235034eb2a9ef4f38f5760465
Source dataset
uspto-grants-1980_06
Patent number
US04209452

Reaction notes

Loading…