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Hydrochloric Acid → 4-Fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate

HRID 1506741
Notes
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Reaction equation

HRID 1506741 reaction equation
[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:15]2[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:17][CH:9]1[CH2:10]3)[CH2:14]2)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl.[Cl-].[F:24][C:25]1[CH:30]=[CH:29][C:28]([S+:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1>C(Cl)Cl.O.O1CCOCC1>[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:9]2[CH2:17][CH:13]3[CH2:12][CH:11]([CH2:16][CH:15]1[CH2:14]3)[CH2:10]2)[C:3]([O-:5])=[O:4].[F:24][C:25]1[CH:30]=[CH:29][C:28]([S+:31]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866496604-Fluorophenyldiphenylsulfonium chlorideHCID 117966647Ethyl difluoro-(2-hydroxy-adamantan-2-yl)acetate

Product 1

HCID 1317343634-Fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetateYield 45%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.6 g of ethyl difluoro-(2-hydroxyadamantan-2-yl)acetate, prepared in Synthesis Example 1-8, 30 g of 1,4-dioxane, 4.0 g of 25 wt % sodium hydroxide, and 10 g of water was stirred for 2 hours. To the reaction solution, 1.0 g of 35 wt % hydrochloric acid was added, and then 66 g of an aqueous solution of 4-fluorophenyldiphenylsulfonium chloride and 100 g of methylene chloride were added. After stirring for 30 minutes, the organic layer was taken out, washed with water, and concentrated under reduced pressure. Methyl isobutyl ketone was added to the concentrate, which was concentrated again. Diisopropyl ether was added to the concentrate. The supernatant was removed, leaving 2.4 g of the target compound, 4-fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate as vitreous solids (yield 45%).

Workup

  1. stirringAfter stirring for 30 minutes
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. additionMethyl isobutyl ketone was added to the concentrate, which
  5. concentrationwas concentrated again
  6. additionDiisopropyl ether was added to the concentrate
  7. customThe supernatant was removed

Sources & evidence

ORD record
ord-fedf4ea1bb7143a6925d2c8584a3b5dd
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221742B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes