Hydrochloric Acid → 1-(2-Chloroethyl)-4-fluorobenzene

HRID 1351541Notes

Reaction equation

HRID 1351541 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.[ClH:11].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>ClC1C=CC=CC=1>[Cl:11][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 820684-Fluorophenethyl AlcoholHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 676221-(2-Chloroethyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 7 g 2-(4-fluoro-phenyl)-ethanol, 25 mL of chlorobenzene, 42 mL of 37% HCl, and 0.9 g of Aliquot® 336 (tricaprylylmethyl ammonium chloride) was heated to reflux for 3 days, cooled and extracted into 3×100 mL of hexane. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was mainly 1-(2-chloro-ethyl)-4-fluoro-benzene:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. temperaturecooled
  4. extractionextracted into 3×100 mL of hexane
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c9be65b8d1a455e87d3baf185718e36
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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