4-Iodophenol → 4',5'-Difluoro-2'-methoxy-biphenyl-4-ol

HRID 547844ノート

反応式

HRID 547844 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5](B(O)O)=[C:4]([O:12][CH3:13])[CH:3]=1.I[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O.[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>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:4]([O:12][CH3:13])[CH:3]=1

参加物

8

反応物 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acid

生成物 1

HCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-ol収率 89.3%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
82.5 °C

実験手順

4,5-Difluoro-2-methoxyphenyl-boronic acid (8.8 g, 46.82 mmol) and 4-iodophenol (6.86 g, 31.21 mmol) were suspended in 165 ml of DMF. H2O (40 mL) was added and the mixture was degassed with argon. Finely ground potassium carbonate (13 g, 93.63 mmol) and tetrakis(triphenylphosphine) palladium(0) (1.5 g, 1.29 mmol) were added. The reaction was stirred at 80-85° C. for 1 hr under argon and cooled. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried and solvents were evaporated. The crude product was purified by flash chromatography, eluting with 0-8% ethyl acetate in hexanes to yield 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol (6.58 g, 89.3%). LR-MS (ES) calculated for C13H10F2O, 236.22; found m/z 235 [M−H]−.

後処理

  1. customthe mixture was degassed with argon
  2. temperaturecooled
  3. washThe organic layer was washed with brine
  4. customdried
  5. customsolvents were evaporated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 0-8% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-ca1b55e1aeb742eca7e378533e6547e1
出典データセット
uspto-grants-2011_05
特許番号
US07939569B1

反応ノート

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