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

HRID 1726384

反応式

HRID 1726384 の反応式
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

参加物

8

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 8150Diglyme溶媒

反応条件

温度
88 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f7d2824e37d748efbaa5e49b5eac6485
出典データセット
uspto-grants-2009_02
特許番号
US07491821B2

関連ノート

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