Acetic Acid → HCID 57565859, compound

HRID 1728116Notes

Reaction equation

HRID 1728116 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][C:3]=1[F:19].C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:30]=[O:31].C(O)(=O)C>O1CCCC1.O>[Br:1][C:2]1[C:3]([F:19])=[C:4]([C:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:15])([CH3:14])[CH3:16])([CH3:11])[CH3:12])=[CH:17][CH:18]=1)[CH:30]=[O:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 57565903HCID 57565903, compound

Product 1

HCID 57565859HCID 57565859, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 52a, 1 [2-(4-bromo-3-fluoro-phenoxy)-ethoxy]-tert-butyl-dimethyl-silane (17.2 g, 49.3 mmol) prepared in example 183a was reacted with lithium diisopropyl amide (32.8 mL, 2.0 M in THF, 59.1 mmol), N,N-dimethyl-formamide (4.57 mL, 59.1 mmol) and quenched with acetic acid (12.1 g, 197.2 mmol) and water (61.8 mL) in tetrahydrofuran to give 3-bromo-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-2-fluoro-benzaldehyde as white solid (Yield: 12 g, 67%).

Sources & evidence

ORD record
ord-40a6709b49454cf39d877fb936cb89a0
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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