Water → HCID 18539369, compound

HRID 1007471Notes

Reaction equation

HRID 1007471 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([Br:26])[C:24]=1O)[CH:20]=[O:21].O>N1C=CC=CC=1>[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([Br:26])[C:24]=1[O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])[CH:20]=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 18539369HCID 18539369, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

14.73 ml of triflic anhydride is added, under inert gas and at 0° C., to 19.0 g of 3,5-dibromo-4-hydroxy-benzaldehyde in 100 ml of pyridine. Agitation is carried out for 1 hour while allowing the temperature to return to ambient, the reaction medium is poured into water and the aqueous phase is extracted with 3 times 150 ml of dichloromethane. The organic phases are dried and evaporated to dryness under reduced pressure. 23.83 g of crude product is obtained which is purified by filtration chromatography using a cyclohexane/ethyl acetate mixture 1/1 as eluant. In this way 23.83 g of expected product is obtained. Rf: 0.71, cyclohexane/ethyl acetate 1/1. The operation is carried out in an equivalent manner for the preparation of the following triflates of general formula II

Workup

  1. extractionthe aqueous phase is extracted with 3 times 150 ml of dichloromethane
  2. customThe organic phases are dried
  3. customevaporated to dryness under reduced pressure
  4. custom23.83 g of crude product is obtained which
  5. filtrationis purified by filtration chromatography

Sources & evidence

ORD record
ord-a6d8a8dea26441e3937ba6d439751526
Source dataset
uspto-grants-2004_09
Patent number
US06794415B2

Reaction notes

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