4-Bromo-2-fluorobenzaldehyde → HCID 63895095, compound

HRID 537454Notes

Reaction equation

HRID 537454 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH2:11]([Mg]Cl)[CH2:12][CH3:13]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:11][CH2:12][CH3:13])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 178455855HCID 178455855, compound

Product 1

HCID 63895095HCID 63895095, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of 4-bromo-2-fluorobenzaldehyde (600 mg, 3 mmol) in tetrahydrofuran (10 mL) was added n-propylmagnesium chloride (2.22 mL, 4.43 mmol) dropwise over 20 minutes. The reaction was warmed to 0° C. and stirred for 2 hours. The reaction was quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate (3×), dried over sodium sulfate, filtered, and concentrated. Purification by preparatory thin layer chromatography gave (+/−)-1-(4-bromo-2-fluorophenyl)butan-1-ol (440 mg, 60%) as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.26-7.30 (m, 1H), 7.21 (d, J=8.0 Hz 1H), 7.13 (d, J=8.0 Hz, 1H), 4.90 (t, J=5.6 Hz, 1H), 1.53-1.79 (m, 2H), 1.30-1.45 (m, 2H), 0.85 (s, J=5.6 Hz, 3H).

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by preparatory thin layer chromatography

Sources & evidence

ORD record
ord-91443dc6be8346f6ba2119a2805af82c
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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