Chloroform → 2-(4-Fluorophenoxy)ethanol

HRID 2051930Notes

Reaction equation

HRID 2051930 reaction equation
B#B.[F:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](O)=[O:11])=[CH:6][CH:5]=1.C(Cl)(Cl)Cl>O1CCCC1>[F:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 678824-Fluorophenoxyacetic acidHCID 6328200Diboron

Product 1

HCID 5743612-(4-Fluorophenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 ml of 1 M diborane in tetrahydrofuran was added dropwise 17.0 L g of 4-fluorophenoxyacetic acid in 100 ml of tetrahydrofuran at 5°-10° C. The reaction was stirred at room temperature overnight and poured into a mixture of 100 ml of ice and 750 ml of chloroform. The water phase was extracted twice more with 250 ml each of chloroform and the combined organic phase dried. This solution was concentrated to a light yellow oil. This material was placed on the Kugelrohr (vacuum distillation) giving 14.8 g on distillation.

Workup

  1. extractionThe water phase was extracted twice more with 250 ml each of chloroform
  2. customthe combined organic phase dried
  3. concentrationThis solution was concentrated to a light yellow oil
  4. distillationThis material was placed on the Kugelrohr (vacuum distillation)
  5. customgiving 14.8 g
  6. distillationon distillation

Sources & evidence

ORD record
ord-cb261b64cce84f7d83c091a809676fe7
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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