Ethylene → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

HRID 890372Notes

Reaction equation

HRID 890372 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:20]=[CH2:21]>ClC(Cl)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH2:8][C:9](=[O:11])[CH2:21][CH2:20]2

Participants

7

Reactant 4

HCID 6325EthyleneHCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-fluorophenylacetic acid (1 equivalent) was dissolved in dichloroethane (1.3 M) containing SOCl2 (3 equivalents), the mixture was refluxed for 90 minutes and the solvent was removed. Solution of this crude product in CH2Cl2 was added dropwise within 60 minutes to AlCl3 (2 eq) in CH2Cl2 (0.4 M) while stirring at 0° C. Thereafter, ethylene was introduced at 0° C. over 45 minutes, whereupon the mixture was stirred further at room temperature for 1 hour, and thereafter was treated at 0° C. with ice-water. The organic phase was washed with 1 N HCl (2×), NaHCO3 (sat. sol.), dried and evaporated. The residue was triturated with hexane, yielding the product as a bright yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customthe solvent was removed
  3. stirringwas stirred further at room temperature for 1 hour
  4. washThe organic phase was washed with 1 N HCl (2×), NaHCO3 (sat. sol.)
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-9b53831fa1fb4b54ae682bbb1bfc52a3
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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