Thionyl Chloride → Methyl 9-chloro-2-fluoro-9H-fluorene-9-carboxylate

HRID 485703Notes

Reaction equation

HRID 485703 reaction equation
[CH3:1][O:2][C:3]([C:5]1(O)[C:17]2[CH:16]=[C:15]([F:18])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4].S(Cl)([Cl:22])=O>>[CH3:1][O:2][C:3]([C:5]1([Cl:22])[C:17]2[CH:16]=[C:15]([F:18])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14579585HCID 14579585, compound

Product 1

HCID 15037271Methyl 9-chloro-2-fluoro-9H-fluorene-9-carboxylate

Procedure

A mixture of 2-fluoro-9-hydroxy-9H-fluorene-9-carboxylic acid methyl ester (5) (4.00 g, 15.5 mmol) and 50 mL thionyl chloride was refluxed 3 h. After the thionyl chloride was removed on the rotavapor, the material was redissolved in 50 mL benzene and the benzene then evaporated to remove trace thionyl chloride. The crude product, 4.3 g (100%), was used without further purification.

Workup

  1. temperaturewas refluxed 3 h
  2. customAfter the thionyl chloride was removed on the rotavapor
  3. dissolutionthe material was redissolved in 50 mL benzene
  4. customthe benzene then evaporated
  5. customto remove trace thionyl chloride
  6. customThe crude product, 4.3 g (100%), was used without further purification

Sources & evidence

ORD record
ord-d10596445fea46bfb69dc366401a5552
Source dataset
uspto-grants-1985_08
Patent number
US04537892

Reaction notes

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