Methyl Thioglycolate → HCID 54383689, compound

HRID 1898953Notes

Reaction equation

HRID 1898953 reaction equation
Br[C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C:21]([O:25][CH3:26])(=[O:24])[CH2:22][SH:23]>C1(C)C=CC=CC=1>[C:15]1([C:2]2([S:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 2316249-Bromo-9-phenylfluorene

Product 1

HCID 54383689HCID 54383689, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 9-bromo-9-phenylfluorene (Aldrich) (1.9 g, 5.9 mmol) and methyl thioglycolate (0.70 mL, 7.8 mmol) in 50 mL of toluene is heated at reflux for 4 hours. The reaction is cooled and concentrated in vacuo. The resulting oil is chromatographed on silica gel eluting with a gradient of ethyl acetate/toluene/hexane (3:20:77 to 5:40:55). The purified product is co-evaporated with hexane 2 times and dried under vacuum for 3 days to give 1.6 g (77%) of methyl (9-phenylfluoren-9-yl-thio)acetate as an oil.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction is cooled
  3. concentrationconcentrated in vacuo
  4. customThe resulting oil is chromatographed on silica gel eluting with a gradient of ethyl acetate/toluene/hexane (3:20:77 to 5:40:55)
  5. customdried under vacuum for 3 days

Sources & evidence

ORD record
ord-3ba4c1303fe349fd818ee1accfa92836
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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