Pyridine → HCID 23077305, compound

HRID 1350607Notes

Reaction equation

HRID 1350607 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:19])[C:16]=2[F:18])[CH:11]=[CH:10][C:9]=1[OH:20].[F:21][C:22]([F:28])([F:27])[S:23](O)(=[O:25])=[O:24]>ClCCl.O>[F:21][C:22]([F:28])([F:27])[S:23]([O:20][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[C:16]([F:18])[C:15]([F:19])=[CH:14][CH:13]=2)[C:8]=1[F:7])(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 230773061,7,8-Trifluoronaphthalen-2-ol

Product 1

HCID 23077305HCID 23077305, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (10 ml) was added slowly and dropwise to a dichloromethane (60 ml) solution of 1,7,8-trifluoro-2-naphthol (10 g) and trifluoromethanesulfonic acid anhydrate (10.3 ml) at the temperature of the ice/water, and then the reaction solution was stirred for 30 minutes. Water and dichloromethane were added slowly in the reaction solution. The organic layer was removed, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water, 10% hydrochloric acid, a saturated sodium hydroxide aqueous solution, water, and brine consecutively, and concentrated. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=19/1), and 1,7,8-trifluoronaphthalene-2-yl trifluoromethanesulfonate was obtained as light yellow crystals.

Workup

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washwashed with water, 10% hydrochloric acid
  4. concentrationa saturated sodium hydroxide aqueous solution, water, and brine consecutively, and concentrated
  5. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-ee7ad5da31a64fbcafa54725ac7d2db7
Source dataset
uspto-grants-2007_05
Patent number
US07214835B2

Reaction notes

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