1-Bromopropane → HCID 63894506, compound

HRID 1880370Notes

Reaction equation

HRID 1880370 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:14])=[C:10]([CH:13]=1)[CH:11]=[O:12]>C(OCC)C.II>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:14])=[C:10]([CH:11]([OH:12])[CH2:1][CH2:2][CH3:3])[CH:13]=1

Participants

5

Reactant 2

HCID 78401-Bromopropane2×HCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 63894506HCID 63894506, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 807IodineSolvent2×HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of Mg (0.236 g, 9.83 mmol) in diethyl ether (10 mL), I2 (1 spatula) was added n-propyl bromide (0.72 g, 0.53 mL, 5.9 mmol) at room temperature. When iodine color disappeared, the remaining n-propyl bromide in ether was added to the reaction mixture and stirred at room temperature for 10 minutes. To this Grignard reagent, 5-bromo-2-fluorobenzaldehyde (1.00 g, 4.92 mmol) in ether was added under cold conditions and stirred at room temperature for 1 hour. The reaction mixture was quenched with NH4Cl solution and extracted with ether. The ether layer was dried over anhydrous Na2SO4, filtered and concentrated to afford 1-(5-bromo-2-fluoro-phenyl)-butan-1-ol (1.14 g, 92.6%). 1H NMR (CDCl3): δ 7.6 (m, 1H), 7.3-7.4 (m, 1H), 6.9 (t, 1H), 5.0 (brs, 1H), 2.0 (brs, 1H), 1.6-1.7 (m, 2H), 1.3-1.5 (m, 2H), 1.0 (t, 3H).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customThe reaction mixture was quenched with NH4Cl solution
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c803bfef0b64c8eba5a984115dc6178
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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