2,2-Difluoro-5-formylbenzodioxole → Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methanol

HRID 561481Notes

Reaction equation

HRID 561481 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3]1.[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.ClC1C=C(F)C(C(C2CC2)O)=C(F)C=1>O1CCCC1>[CH:14]1([CH:11]([C:9]2[CH:8]=[CH:7][C:5]3[O:6][C:2]([F:1])([F:13])[O:3][C:4]=3[CH:10]=2)[OH:12])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 27369732,2-Difluoro-5-formylbenzodioxoleHCID 58392245(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methanolHCID 178418630HCID 178418630, compound

Product 1

HCID 58392116Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared starting from 3.50 g (18.81 mmol) of 2,2-difluoro-5-formylbenzodioxolane and 56.4 ml (28.21 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran in analogy to the synthesis of the compound from Example 156A. 1.59 (37% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-509e347e6f664567bf31646d9940493f
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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