2-Amino-6-chlorobenzaldehyde → (+/-)-(2-Amino-6-chlorophenyl)-(4-fluorophenyl)methanol

HRID 2117277Notes

Reaction equation

HRID 2117277 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:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1>C(OCC)(=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1)[OH:5]

Participants

4

Reactant 2

HCID 223995122-Amino-6-chlorobenzaldehydeHCID 178418676HCID 178418676, compound

Product 1

HCID 69315535(+/-)-(2-Amino-6-chlorophenyl)-(4-fluorophenyl)methanolYield 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 4-fluorophenylmagnesium bromide (1 M in THF, 3.8 mL) to afford 0.28 g (57%) of (±)-(2-amino-6-chlorophenyl)-(4-fluorophenyl)methanol after flash chromatography (4:1 hexanes:ethyl acetate).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-ab9d8f78d16f40d3a2cbdea772ddc349
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Reaction notes

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