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Cesium fluoride → 4-(4'-Chloro-4-ethyl-2'-fluorobiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione

HRID 1191557
Notes
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Reaction equation

HRID 1191557 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH:7]=1.[F-].[Cs+].[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[C:27]([F:34])[CH:26]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]3[C:9](=[O:19])[C:10]([CH3:18])([CH3:17])[O:11][C:12]([CH3:15])([CH3:16])[C:13]3=[O:14])[CH:7]=2)=[C:27]([F:34])[CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 4193595(4-Chloro-2-fluorophenyl)boronic acidHCID 666785694-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 532355474-(4'-Chloro-4-ethyl-2'-fluorobiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dioneYield 77.9%

Reagents, catalysts & solvents 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.278 g, 0.79 mmol), cesium fluoride (1.19 g, 7.90 mmol), 4-chloro-2-fluorophenylboronic acid (0.194 g, 1.11 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.102 g, 0.12 mmol) is added degassed dimethoxyethane (2 ml), and the resulting suspension is stirred under nitrogen for 45 minutes then heated at 80° C. for 20 hours. After cooling to room temperature the reaction mixture is partitioned between ethyl acetate and 1M aqueous hydrochloric acid. The aqueous phase is further extracted with ethyl acetate, then all organic fractions are combined, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting material is purified by column chromatography on silica gel (hexane/ethyl acetate 3:1 ratio) to afford 4-(4′-chloro-4-ethyl-2′-fluorobiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione (0.248 g) as a white solid.

Workup

  1. additionis added
  2. customdegassed dimethoxyethane (2 ml)
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. customis partitioned between ethyl acetate and 1M aqueous hydrochloric acid
  5. extractionThe aqueous phase is further extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting material is purified by column chromatography on silica gel (hexane/ethyl acetate 3:1 ratio)

Sources & evidence

ORD record
ord-738bbba361184691a16413f8d5ddfbf7
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680012B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes