Potassium Carbonate → 4-(4-Bromo-3-fluoro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1095074Notes

Reaction equation

HRID 1095074 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:10][C:7]2[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([F:11])[C:4]=2[CH:5]=[O:6])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 577433543-Bromo-2-fluoro-6-hydroxybenzaldehyde

Product 1

HCID 577434454-(4-Bromo-3-fluoro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 4a, 3-bromo-2-fluoro-6-hydroxy-benzaldehyde (3.69 g, 16.8 mmol) reacted with 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (4 g, 11.2 mmol, ASTATECH) and K2CO3 in N,N-dimethylformamide to give 4-(4-bromo-3-fluoro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester as a brown oil (Yield 4.23 g, 94%).

Sources & evidence

ORD record
ord-41c50e67052145c68ed2f2745e79408f
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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