4-Chloro-alpha-cyclopropylbenzenemethanol → 2-Chloro-alpha-cyclopropyl-4-fluorobenzenemethanol

HRID 561479Notes

Reaction equation

HRID 561479 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.C1(C(C2C=CC(Cl)=CC=2)O)CC1>O1CCCC1>[CH:11]1([CH:4]([C:3]2[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=2[Cl:1])[OH:5])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 866794-Chloro-alpha-cyclopropylbenzenemethanolHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 583924042-Chloro-alpha-cyclopropyl-4-fluorobenzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared starting from 1.50 g (9.46 mmol) of 2-chloro-4-fluorobenzaldehyde and 28.4 ml (14.19 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran in analogy to the synthesis of the compound from Example 153A. 1.51 g (80% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-832ea3baacfc4683ad1b791dacb9a363
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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