Acetic Acid → 2,3-Difluoro-6-(2-methoxyethoxy)benzaldehyde

HRID 1728041Notes

Reaction equation

HRID 1728041 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]=1[F:13].C(NC(C)C)(C)C.[Li].CN(C)[CH:24]=[O:25].C(O)(=O)C>O1CCCC1.O>[F:13][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])[C:4]=1[CH:24]=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 45051747Lithium diisopropylamineHCID 574290663,4-Difluoro-1-(2-methoxyethoxy)benzene

Product 1

HCID 575658102,3-Difluoro-6-(2-methoxyethoxy)benzaldehydeYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, 1,2-difluoro-4-(2-methoxy-ethoxy)-benzene (6.3 g, 33.4 mmol) prepared in example 101a was reacted with lithium diisopropylamine (20.1 mL, 2.0 M in THF, 40.1 mmol), N,N-dimethyl-formamide (3.11 mL, 40.1 mmol) and quenched with acetic acid (8.1 g, 134 mmol) and water (41.2 mL) in tetrahydrofuran to give 2,3-difluoro-6-(2-methoxy-ethoxy)-benzaldehyde as yellow oil (Yield: 5.8 g, 80.6%).

Sources & evidence

ORD record
ord-be89e56bb3634ea9b3e19aee7d471dc9
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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