Sulfuric Acid → 7-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine

HRID 452459Notes

Reaction equation

HRID 452459 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.[Br:12][CH2:13][CH:14](OC)OC.OS(O)(=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]2[CH2:9][O:10][CH:14]([CH2:13][Br:12])[O:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 671557215-Bromo-3-fluoro-2-(hydroxymethyl)phenol

Product 1

HCID 671556997-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation according to Preparation 9. 5-bromo-3-fluoro-2-(hydroxymethyl)phenol (0.79 g, 3.6 mmol), 2-bromo-1,1-dimethoxyethane (4.2 ml, 36 mmol), dry THF (10 ml) and concentrated H2SO4 (1.5 ml).

Workup

  1. customPreparation
  2. customaccording to Preparation 9

Sources & evidence

ORD record
ord-d75b2f305a0f40e39e72939ed22c835b
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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