2-Amino-6-chlorobenzaldehyde → (+/-)-1-(2-Amino-6-chlorophenyl)-2-(3,4-difluorophenyl)ethanol

HRID 2117280Notes

Reaction equation

HRID 2117280 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[O:5].[F:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:15][Mg]Br>C(OCC)(=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]([OH:5])[CH2:15][C:14]1[CH:18]=[CH:19][C:20]([F:21])=[C:12]([F:11])[CH:13]=1

Participants

4

Reactant 2

HCID 223995122-Amino-6-chlorobenzaldehydeHCID 178505753HCID 178505753, compound

Product 1

HCID 69318113(+/-)-1-(2-Amino-6-chlorophenyl)-2-(3,4-difluorophenyl)ethanolYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared using General Method 1 (EXAMPLE 1) from 2-amino-6-chlorobenzaldehyde (0.30 g, 1.9 mmol) and 3,4-difluorobenzylmagnesium bromide (generated from 3,4-difluorobenzyl bromide and magnesium in ether, 3.9 mmol, 2 equiv) to afford 0.28 g (57%) of (±)-1-(2-amino-6-chlorophenyl)-2-(3,4-difluorophenyl)ethanol after flash chromatography (4:1 hexanes:ethyl acetate).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-c187a39e288e4920babc609538a053d3
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Reaction notes

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