Hydrogen Bromide → 2-Fluorophenethyl bromide

HRID 362836

Reaction equation

HRID 362836 reaction equation
[BrH:1].S(=O)(=O)(O)O.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15]O>>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][Br:1]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 27569642-Fluorophenethyl bromideYield 99%

Procedure

To a mixture of aqueous hydrobromic acid (48%, 360 mL) and concentrated sulfuric acid (103.6 mL) at room temperature was added dropwise 2-(2-fluorophenyl)ethanol (250 g, 1.78 mol, Aldrich). The reaction mixture was refluxed for 7 h, poured onto 600 ml of ice and the mixture was extracted with diethyl ether. The diethyl ether extracts were washed successively with saturated sodium carbonate and brine. The organic phase was dried (MgSO4) and concentrated in vacuo to give 359.9 g (99%) of 2-(2-fluorophenyl)-ethylbromide as a brown oil. This product was used without further purification. NMR (CDCl3 : d 7.6-6.9 (m. 4H, ArH), 3.6 (t, 2H CH2), 3.2 (t, 2H, CH2).

Workup

  1. temperatureThe reaction mixture was refluxed for 7 h
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe diethyl ether extracts were washed successively with saturated sodium carbonate and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94c84f6978a34477bbb058ea20e1f0a0
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Linked notes

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