Iodoethane → 1-(4-Bromo-2-fluorophenyl)propan-1-ol

HRID 1476185Notes

Reaction equation

HRID 1476185 reaction equation
[CH2:1]([Mg]I)[CH3:2].[Mg].C(I)C.[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([F:18])[CH:11]=1>C(OCC)C>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH2:1][CH3:2])=[C:12]([F:18])[CH:11]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224MagnesiumHCID 178461634HCID 178461634, compound

Product 1

HCID 638950941-(4-Bromo-2-fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a ice-cold solution of ethyl magnesium iodide prepared from magnesium (2.39 g, 98.51 mmoles) and ethyl iodide (7.88 ml, 98.51 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 (5.8 g, 99% yield) which is used as such for step.

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-889589da925f4dbba4acc1b74b177c08
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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