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

HRID 854304

Reaction equation

HRID 854304 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]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].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 2

HCID 313Hydrochloric AcidHCID 820684-Fluorophenethyl Alcohol

Product 1

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

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 7 g of 2-(4-fluoro-phenyl)-ethanol, 25 mL of chlorobenzene, 42 mL of 37% HCl, and 0.9 g of Aliquat® 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 a crude product of 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-87d0ef2d4e4141fea3a30bece2afa79d
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Linked notes

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