Sodium Carbonate → Methyl 3-bromo-5-(4-fluorophenyl)benzoate

HRID 1726384

반응식

HRID 1726384 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOCCOC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 621923Methyl 3,5-Dibromobenzoate

생성물 2

HCID 69062042Methyl 3,5-di(4-fluorophenyl)benzoate수율 4%HCID 69068418Methyl 3-bromo-5-(4-fluorophenyl)benzoate수율 23%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 8150Diglyme용매

반응 조건

온도
88 °C

실험 절차

To a solution of methyl 3,5-dibromobenzoate (3.00 g, 10.2 mmol) and 4-fluoro-phenyl boronic acid (1.43 g, 10.2 mmol) in 2-methoxyethyl ether (60 ml) and ethanol (3 ml) was added Na2CO3 (saturated, 9 ml), followed by tetrakis(triphenylphosphine) palladium (0) (0.2 g). The mixture was heated at 88° C. for 1.5 h, then cooled to room temperature, partitioned between hexane and water, and the organic phase washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to yield methyl 3-bromo-5-(4-fluorophenyl)benzoate (intermediate XXXIVa, 0.725 g, 23%) as a white solid, and methyl 3,5-di(4-fluorophenyl)benzoate (intermediate XXXIVb, 0.128 g, 4%) as a white solid.

후처리

  1. temperaturecooled to room temperature
  2. custompartitioned between hexane and water
  3. washthe organic phase washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationthe organic solution concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-f7d2824e37d748efbaa5e49b5eac6485
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491821B2

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