Sodium Carbonate → HCID 18451490, 화합물

HRID 1270711

반응식

HRID 1270711 반응식
[F:1][C:2]1[C:8]([F:9])=[C:7](Br)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C(O)C>[F:1][C:2]1[C:8]([F:9])=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 6186714-Bromo-2,3,5,6-tetrafluoroaniline

생성물 1

HCID 18451490HCID 18451490, 화합물

시약·촉매·용매 2

HCID 241Benzene용매HCID 702Ethanol용매

실험 절차

2,3,5,6-Tetrafluoro-4-bromoaniline (13.8 g, 56.7 mmol) is dissolved in benzene (200 mL) and treated with 1.5 equivalents of phenylboronic acid (10.4 g, 85.1 mmol) and a catalytic amount of tetrakistriphenylphosphine palladium(0) (4.2 g, 3.6 mmol) as a solution in ethanol (30 mL). Sodium carbonate (60 mL of 2 M aqueous solution) is added and the reaction mixture stirred and heated to reflux temperature for 24 hours. After cooling to room temperature the mixture is partitioned between Et2O (500 mL) and water (250 mL). The organic layer is washed with brine, dried (MgSO4) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-phenylaniline as an oil.

후처리

  1. temperatureheated
  2. temperatureto reflux temperature for 24 hours
  3. customis partitioned between Et2O (500 mL) and water (250 mL)
  4. washThe organic layer is washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated by rotary evaporator
  7. customThe residual oil is purified by flash chromatography (9:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-efd0175ca527483b827db0d3a68e28bf
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202364B2

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