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

HRID 2413473Notes

Reaction equation

HRID 2413473 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-532216904fb6448fb75cfd62867974be
Source dataset
uspto-grants-1988_01
Patent number
US04717725

Reaction notes

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