Thionyl Chloride → 1,1'-(3-Chloropropylidene)bis(4-fluorobenzene)

HRID 257435Notes

Reaction equation

HRID 257435 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10]O)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>ClCCl>[Cl:21][CH2:10][CH2:9][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 197832883,3-Bis(4-fluorophenyl)propanol

Product 1

HCID 197832871,1'-(3-Chloropropylidene)bis(4-fluorobenzene)Yield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.5 parts of 3,3-bis(4-fluorophenyl)-1-propanol and 2.92 parts of thionyl chloride in 39.9 parts of dichloromethane was stirred for 4 hours at 60° C. The reaction mixture was evaporated and then co-evaporated with methylbenzene. The residue was dissolved in ethyl acetate and this solution was washed with Na2CO3 (aq.), water and NaCl (sat.) and was then dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; (C2H5)2O/n. hexane 2:98). The eluent of the desired fraction was evaporated, yielding 4.5 parts (76.7%) of 1-[3-chloro-1-(4-fluorophenyl)propyl]-4-fluorobenzene (interm. 22).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthis solution was washed with Na2CO3 (aq.), water and NaCl (sat.)
  4. customwas then dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; (C2H5)2O/n. hexane 2:98)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-9b591b3cab8e4c3d81f1135ef2ca766c
Source dataset
uspto-grants-1993_11
Patent number
US05262418

Reaction notes

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