5-Bromo-2-fluorobenzaldehyde → 1-(5-Bromo-2-fluorophenyl)propan-1-ol

HRID 1880374Notes

Reaction equation

HRID 1880374 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][CH2:12][Mg+].[Br-]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]([OH:8])[CH2:11][CH3:12])[CH:9]=1

Participants

4

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 589415561-(5-Bromo-2-fluorophenyl)propan-1-olYield 105.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (10 g, 49 mmol) in diethyl ether (20 mL) at 15° C., was added drop wise at 15° C. EtMgBr (7.22 g, 54.2 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with cold water and NH4Cl solution. It was extracted with diethyl ether and the ether layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under vacuum to afford 1-(5-bromo-2-fluorophenyl)propan-1-ol (12.1 g, 98%) as a syrup. 1H NMR (CDCl3): δ 7.6-7.7 (m, 1H), 7.2-7.3 (m, 1H), 6.9 (t, 1H), 4.9 (brs, 1H), 1.8 (m, 2H), 1.0 (t, 3H).

Workup

  1. customThe reaction mixture was quenched with cold water and NH4Cl solution
  2. extractionIt was extracted with diethyl ether
  3. washthe ether layer was washed with saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d34598a244844855837c027491cede31
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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