Acetic Acid → HCID 57566152, compound

HRID 1728044Notes

Reaction equation

HRID 1728044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH3:11])=[CH:4][C:3]=1[F:12].CN(C)[CH:15]=[O:16].C(O)(=O)C.O>O1CCCC1.C(NC(C)C)(C)C.[Li]>[F:12][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([O:8][CH2:9][CH2:10][CH3:11])[C:4]=1[CH:15]=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6228DimethylformamideHCID 53857878HCID 53857878, compound

Product 1

HCID 57566152HCID 57566152, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 45051747Lithium diisopropylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, 1,2-difluoro-4-propoxy-benzene (17 g, 98.8 mmol) prepared in example 104a was reacted with lithium diisopropyl amine (59.2 mL, 2.0 M in THF, 0.118 mmol), N,N-dimethyl-formamide (9.17 mL, 0.118 mol) and quenched with acetic acid (23.7 g, 0.395 mol) and water (41.2 mL) in tetrahydrofuran to give 2,3-difluoro-6-propoxy-benzaldehyde as a yellow solid (Yield: 8.2 g, 42%).

Sources & evidence

ORD record
ord-1696e27432b044548427c10cddfc44ca
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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