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

HRID 2410472
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HRID 2410472 반응식
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
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참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 962Water용매
HCID 15413tert-Butyl methyl ether용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0cf5d2f1c2c84bc3b2a455209f39cd07
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815919B2

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