Sulfate Ion → HCID 18782495, compound

HRID 1420821Notes

Reaction equation

HRID 1420821 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[S:14]([O-:18])([O-])(=O)=[O:15]>N1C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[S:14]([O:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[Br:1])(=[O:18])=[O:15]

Participants

4

Reactant 2

HCID 1117Sulfate IonHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 18782495HCID 18782495, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled (0° C.) solution of 2-bromo-4-(trifluoromethoxy)phenol (Description 11, 10 g, 40 mmol) in pyridine (20 ml), was added trifluooromethanesulphonic anhydride (7.2 ml, 44 mmol), and the reaction was stirred at ambient temperature for 2 h. The reaction was diluted with saturated cooper (II) sulphate (80 ml) and extracted into ethyl acetate (3×60 ml). The combined organic fractions were washed with water (80 ml), brine (80 ml), dried (MgSO4) and evaporated in vacuo. Purification on silica, eluting with hexane gave the title compound as a clear oil (13.1 g, 85%). 1H NMR (250 MHz, CDCl3) δ7.28 (1H, m), 7.40 (1H, d, J 9.1 Hz), and 7.58 (1H, d, J 2.8 Hz).

Workup

  1. extractionextracted into ethyl acetate (3×60 ml)
  2. washThe combined organic fractions were washed with water (80 ml), brine (80 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customPurification on silica
  6. washeluting with hexane

Sources & evidence

ORD record
ord-5d625e63447d4209a44b8e0d2378c399
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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