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Potassium Carbonate → [8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

HRID 902328
Notes
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Reaction equation

HRID 902328 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16](Br)[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[Cl:25])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 86609107(8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609118[8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonateYield 53%

Reagents, catalysts & solvents 3

HCID 10876480
Bis(tri-o-tolylphosphine)palladium(II) Dichloride
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (8-bromo-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate, prepared in Example 37, step 5 (1.0 g, 2.42 mmol) and 2-chlorophenylboronic acid (1.14 g, 7.26 mmol) in dioxane (18 mL) was added a solution of potassium carbonate (1.0 g, 7.26 mmol) in water (6 mL) and the mixture purged with nitrogen for 20 minutes. Trans-dichlorobis(tri-o-tolylphosphine)palladium (II) (95 mg, 0.12 mmol) was added and the reaction mixture heated at 100° C. for 2 hours. The cooled reaction mixture was then partitioned between ethyl acetate (100 mL) and 2.0 M aqueous sodium hydroxide (100 mL). The organic layer was separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 5 to 20% ethyl acetate in hexane gave 0.57 g (53%) of [8-(2-chlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a white solid. HRMS: calcd for C23H18ClFO4S+NH4+, 462.09366. found (ESI, [M+NH4]+), 462.0916.

Workup

  1. customthe mixture purged with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. customwas then partitioned between ethyl acetate (100 mL) and 2.0 M aqueous sodium hydroxide (100 mL)
  4. customThe organic layer was separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a yellow oil
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-46abf995a311477fb67fab9f5008980a
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365095B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes