2-Fluorophenol → 4-(5-(tert-butyldimethylsilyloxy)-2-fluoro-alpha-hydroxybenzyl)-N,N-diethylbenzamide

HRID 1460094

Reaction equation

HRID 1460094 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[F:16]C1C=CC=CC=1O.C([Li])(CC)C.[CH:29]([C:31]1[CH:43]=[CH:42][C:34]([C:35]([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[O:36])=[CH:33][CH:32]=1)=[O:30]>ClCCl.CO>[Si:9]([O:8][C:3]1[CH:4]=[CH:5][C:6]([F:16])=[C:7]([CH:2]=1)[CH:29]([C:31]1[CH:43]=[CH:42][C:34]([C:35]([N:37]([CH2:38][CH3:39])[CH2:40][CH3:41])=[O:36])=[CH:33][CH:32]=1)[OH:30])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 97072-FluorophenolHCID 597214tert-Butyl(2-fluorophenoxy)dimethylsilaneHCID 10954698N,N-diethyl-4-formylbenzamideHCID 178418400CID 53628100

Product 1

HCID 541141914-(5-(tert-butyldimethylsilyloxy)-2-fluoro-alpha-hydroxybenzyl)-N,N-diethylbenzamideYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl 2-fluorophenyl ether (2.73 g, 12 mmol), prepared from 2-fluorophenol by the method in Example 1, was treated with sec-butyllithium (11 mL of 1.1M solution in cyclohexane) and 4-formyl-N,N-diethylbenzamide, (2.46 g, 12 mmol) from Example 11, by the procedure described in Example 29. Chromatography on silica gel with 1% methanol in dichloromethane gave 1.77 g (34%) of 4-(5-(tert-butyldimethylsilyloxy)-2-fluoro-α-hydroxybenzyl)-N,N-diethylbenzamide as a yellow oil that crystallized on standing.

Sources & evidence

ORD record
ord-b52f92addf7a435eb1ef7d93defd9f26
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Linked notes

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