Acetic Acid → HCID 57566089, compound

HRID 1728017Notes

Reaction equation

HRID 1728017 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[F:12].C(NC(C)C)(C)C.[Li].CN(C)[CH:23]=[O:24].C(O)(=O)C>O1CCCC1>[F:12][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([O:8][CH:9]([CH3:10])[CH3:11])[C:4]=1[CH:23]=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 27741951,2-Difluoro-4-isopropoxybenzeneHCID 45051747Lithium diisopropylamine

Product 1

HCID 57566089HCID 57566089, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, 1,2-difluoro-4-isopropoxy-benzene (5.77 g, 33.5 mmol) prepared in example 62a was reacted with lithium diisopropyl amine (20.5 mL, 1.8 M in THF, 36.9 mmol), N,N-dimethyl-formamide (3.11 mL, 40.2 mmol) and quenched with acetic acid (8.0 g, 134 mmol) in tetrahydrofuran to give 2,3-difluoro-6-isopropoxy-benzaldehyde as a white crystal (Yield: 6.02 g, 89.9%).

Sources & evidence

ORD record
ord-9282dafd30c8404489b1545eadc6fd53
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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