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Cesium fluoride → Methyl 3'-fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylate

HRID 2410472
Notes
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Reaction equation

HRID 2410472 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].[F:15][C:16]1[C:17]([CH3:34])=[C:18](C2C=CC(C(O)=O)=CC=2COC)[CH:19]=[CH:20][CH:21]=1.FC1C(C)=C(B(O)O)C=CC=1.[F-].[Cs+]>O1CCOCC1.CC(OC)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:15][C:16]1[C:17]([CH3:34])=[C:18]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH2:12][O:13][CH3:14])[CH:19]=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 25953Cesium fluorideHCID 27831913-Fluoro-2-methylphenylboronic AcidHCID 580663983'-Fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

Product 1

HCID 58554131Methyl 3'-fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst
HCID 962WaterSolvent
HCID 15413tert-Butyl methyl etherSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 1, Step 2, 5.00 g, 19.3 mmol), 3-fluoro-2-methylphenylboronic acid (4.46 g, 29.0 mmol), bis(triphenylphosphine)palladium(II) chloride (271 mg, 0.39 mmol) and cesium fluoride (8.79 g, 57.9 mmol) was prepared in dioxane (50 mL) and water (20 mL) under nitrogen atmosphere. The reaction mixture was heated at 100° C. for 1 hour. The reaction mixture was cooled at RT, diluted with MTBE (250 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL). The aqueous layers were extracted with MTBE (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. After purification by flash chromatography (silica, EtOAc/n-hexane), the title compound was obtained as a colorless oil (4.85 g, 87%). HPLC (Method A), Rt 5.0 min (purity: 99.5%). LC/MS (Method B): 289.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled at RT
  2. customthe layers were separated
  3. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  4. extractionThe aqueous layers were extracted with MTBE (150 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by flash chromatography (silica, EtOAc/n-hexane)

Sources & evidence

ORD record
ord-0cf5d2f1c2c84bc3b2a455209f39cd07
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815919B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes