Dimethylformamide → 3-Butyl-5-fluorobenzaldehyde

HRID 20459Notes

Reaction equation

HRID 20459 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](Br)[CH:3]=1.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].CN(C)[CH:17]=[O:18]>C(OCC)C>[CH2:10]([C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH:17]=[O:18])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1370031,3-Dibromo-5-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 862366793-Butyl-5-fluorobenzaldehydeYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve 1,3-Dibromo-5-fluoro-benzene (12.00 g, 0.05 mmol) in diethyl ether (470 mL) and cool to −78 C. Slowly add 1.6 M n-butyllithium in hexanes (29.5 mL, 49.6 mmol) and stir at −78 for one hour. Add dimethylformamide (3.45 g, 0.05 mmol) dropwise and warm to room temperature overnight. Quench with saturated aqueous ammonium chloride solution. Separate the layers and extract the organic layer (1×300 mL) with diethyl ether. Combine the organic layers and wash (1×150 mL) with water, (1×100 μL) with saturated aqueous sodium chloride and dry over magnesium sulfate. Purify using medium pressure chromatography (silica gel, 0-10% diethyl ether:hexanes) to give the desired product (4.15 g, 43%) as a yellow liquid.

Workup

  1. temperaturecool to −78 C
  2. customQuench with saturated aqueous ammonium chloride solution
  3. customSeparate the layers
  4. extractionextract the organic layer (1×300 mL) with diethyl ether
  5. washwash (1×150 mL) with water, (1×100 μL) with saturated aqueous sodium chloride
  6. dry with materialdry over magnesium sulfate
  7. customPurify

Sources & evidence

ORD record
ord-c476a40dfe7e47f582869f13e0b36cae
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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