Acetic Acid → 6-Ethoxy-2,3-difluorobenzaldehyde

HRID 1728034Notes

Reaction equation

HRID 1728034 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([F:11])[CH:5]=1)[CH3:2].C(NC(C)C)(C)C.[Li].CN(C)[CH:22]=[O:23].C(O)(=O)C>O1CCCC1>[CH2:1]([O:3][C:4]1[C:5]([CH:22]=[O:23])=[C:6]([F:11])[C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 27741874-Ethoxy-1,2-difluorobenzeneHCID 45051747Lithium diisopropylamine

Product 1

HCID 107261946-Ethoxy-2,3-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, 4-ethoxy-1,2-difluoro-benzene (10 g, 63 mmol) prepared in example 91a was reacted with lithium diisopropylamine (39 mL, 1.8 M in THF, 70 mmol), N,N-dimethylformamide (5.88 mL, 76 mmol) and quenched with acetic acid (15.2 g, 253 mmol) in tetrahydrofuran to give 6-ethoxy-2,3-difluoro-benzaldehyde as a off white solid (Yield: 8.9 g, 76%).

Sources & evidence

ORD record
ord-0451c38a16a8429a9a56a5c3831ed016
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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