Sodium Carbonate → 2,3',4',5'-Tetrafluorobiphenyl-4-ol

HRID 2239198ノート

反応式

HRID 2239198 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](OB(O)O)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 18180031Water 1,2-dimethoxyethaneHCID 21870694HCID 21870694、化合物

生成物 1

HCID 210521442,3',4',5'-Tetrafluorobiphenyl-4-ol収率 81.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Firstly, 75.0 g of 4-bromo-3-fluorophenol (S3-1), 82.9 g of 3,4,5-trifluoro-phenylboric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, heated to 80° C., and stirred for 4 hours. Next, the reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water. Afterwards, the solution was dried with magnesium sulphate, and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with heptane/ethyl acetate (4/1) as an eluent, and then dried under reduced pressure. The obtained residue was recrystallized in heptane, to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of compound (S3-3) from (S3-1) was 81.5%.

後処理

  1. temperatureNext, the reaction solution was cooled to room temperature
  2. washwashed with 1N HCl(aq) and water
  3. dry with materialAfterwards, the solution was dried with magnesium sulphate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customSubsequently, the product was purified by silica-gel column chromatography with heptane/ethyl acetate (4/1) as an eluent
  7. customdried under reduced pressure
  8. customThe obtained residue was recrystallized in heptane

出典と根拠

ORDレコード
ord-fa252bcab4994fc8a691ab0ce5a151eb
出典データセット
uspto-grants-2010_05
特許番号
US07722783B2

反応ノート

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