Methyl iodide → 1-(4-Bromo-2-fluorophenyl)ethanol

HRID 239633Notes

Reaction equation

HRID 239633 reaction equation
C[Mg]I.[Mg].[CH3:5]I.[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1>C(OCC)C>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([OH:13])[CH3:5])=[C:10]([F:16])[CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224MagnesiumHCID 178418373HCID 178418373, compound

Product 1

HCID 596944341-(4-Bromo-2-fluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 73.88 mmoles) and methyl iodide (4.58 ml, 73.88 mmoles) in diethyl ether (50 ml), 4-bromo-2-fluorobenzaldehyde(5 g, 24.62 mmoles) in diethyl ether(10 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as red colour liquid (5 g, 94% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.40(t, J=8.2 Hz, 1H), 7.30(dd, J=8.3,1.7 Hz, 1H), 7.21(dd, J=9.9,1.9 Hz, 1H), 5.17(q, J=6.4 Hz, 1H), 1.49(d, J=6.5 Hz, 3H).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-686d52f15c2b49d3b5ee8ba33c5d5f54
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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