Water → 2-Chloro-6-fluoro-3-(2-methoxy-ethoxy)-benzaldehyde

HRID 253443Notes

Reaction equation

HRID 253443 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][O:12][CH3:13].C([Li])CCC.CN(C)[CH:21]=[O:22].O>O1CCCC1>[Cl:1][C:2]1[C:3]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:5]=[C:6]([F:8])[C:7]=1[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 178216442-Chloro-4-fluoro-1-(2-methoxyethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 598038162-Chloro-6-fluoro-3-(2-methoxy-ethoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-chloro-4-fluoro-1-(2-methoxy-ethoxy)-benzene (122, 1.50 g, 7.33 mmol) in tetrahydrofuran (44.0 mL), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.08 mL) was added slowly. After 15 minutes, N,N-dimethylformamide (0.681 mL, 8.80 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a light yellow solid (123, 1.20 g, 70.4%).

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexane
  8. customto give a light yellow solid (123, 1.20 g, 70.4%)

Sources & evidence

ORD record
ord-4607fd2d324b423fa4e3a7cccac77e63
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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