Tetrahydrofuran → HCID 86688558, compound

HRID 40574Notes

Reaction equation

HRID 40574 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:19]=[CH:18][C:8]([CH:9]=[N:10]S(C(C)(C)C)(=O)=O)=[CH:7][C:6]=1[F:20].C1C[O:24][CH2:23][CH2:22]1>>[Br:4][C:5]1[CH:19]=[CH:18][C:8]([CH:9]([NH:10][C:23](=[O:24])[CH3:22])[CH3:1])=[CH:7][C:6]=1[F:20]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 866885562-Methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamideHCID 178418573HCID 178418573, compound

Product 1

HCID 86688558HCID 86688558, compound

Procedure

Under inert gas atmosphere 37.2 mL (112 mmol) of a 3N solution of methyl magnesium bromide in THF are added dropwise to 17.1 g (55.8 mmol) 2-methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamide (IX.1) in 170 mL THF at −78° C. The cooling bath is removed and stirring is continued for 2 h. After that time, the mixture is poured into sat. NH4Cl-solution (300 mL) and extracted with EtOAc.

Workup

  1. customThe cooling bath is removed
  2. additionAfter that time, the mixture is poured into sat. NH4Cl-solution (300 mL)
  3. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-ab8ebeff19184249a3edc8fa6e154985
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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