Sulfuric Acid → HCID 67155666, compound

HRID 452453Notes

Reaction equation

HRID 452453 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[CH:5][C:4]=1[OH:16].[Br:17][CH2:18][CH:19](OC)OC.OS(O)(=O)=O>C1COCC1>[Br:17][CH2:18][CH:19]1[O:16][C:4]2[CH:5]=[C:6]([S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[CH:7]=[CH:8][C:3]=2[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 816722-Bromo-1,1-dimethoxyethane2×HCID 66887419HCID 66887419, compound

Product 1

HCID 67155666HCID 67155666, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Preparation according to Preparation 9. 2-(hydroxymethyl)-5-[(trifluoromethyl)sulfonyl]phenol (2.7 g, 10.5 mmol), 2-bromo-1,1-dimethoxyethane (3.0 ml, 25.4 mmol), conc. H2SO4 (1.0 ml), THF (20 ml). Heating at 50° C. for 6 h. Additional 2-bromo-1,1-dimethoxyethane (5×0.5 ml, 21.1 mmol) and conc. H2SO4 (3×1.0 ml) were added during the reaction. Purification by flash column chromatography gave the title compound (3.3 g). MS m/z (rel. intensity, 70 eV) 362 (M+, 5), 360 (M+, 5), 267 (bp), 238 (64), 141 (52), 77 (55).

Workup

  1. customPreparation
  2. customaccording to Preparation 9
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-b671025e55a94f07a11632935813e42a
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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