Sulfuric Acid → 7-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxine

HRID 452465Notes

Reaction equation

HRID 452465 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[CH:4][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[C:3]([F:11])=[CH:4][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 671560275-Bromo-4-fluoro-2-(hydroxymethyl)phenol

Product 1

HCID 671557797-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxineYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation according to Preparation 9. 5-bromo-4-fluoro-2-(hydroxymethyl)phenol (2.3 g, 10.4 mmol), 2-bromo-1,1-dimethoxyethane (9.9 ml, 83 mmol), dry THF (30 ml) and concentrated H2SO4 (4 ml) were heated at 55° C. for 2 h. Purification by flash column chromatography (isooctane/EtOAc 10:1) gave the title compound (1.55 g). MS m/z (rel. intensity, 70 eV) 328 (M+, 11), 326 (M+, 23), 324 (M+, 12) 204 (98), 202 (bp), 176 (41), 174 (43), 95 (59).

Workup

  1. customPreparation
  2. customaccording to Preparation 9
  3. customPurification by flash column chromatography (isooctane/EtOAc 10:1)

Sources & evidence

ORD record
ord-7e8a402645ce424bbff8b89cb5f8f6b3
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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