Chloroform → 2-(4-Fluorophenoxy)ethanol

HRID 1704151Notes

Reaction equation

HRID 1704151 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)ethanolYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 ml of 1 Molar diborane in tetrahydrofuran (chilled to 5°-10° C.) is added dropwise 17.0 g of 2-(p-fluorophenoxy)acetic acid in 100 ml of tetrahydrofuran. The mixture is stirred overnight and poured into 100 g of ice and 250 ml of chloroform. The organic layer is separated and the aqueous layer extracted with chloroform. The organic layer and extracts are combined, dried (MgSO4) and the solvent removed under vacuum. The residual pale yellow oil is distilled to give the product (14.8 g) as a colorless oil.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer extracted with chloroform
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under vacuum
  5. distillationThe residual pale yellow oil is distilled

Sources & evidence

ORD record
ord-664b6583897540ebad1f23758cb384ce
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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