Potassium Phosphate, Tribasic → 4-(4-bromo-3,5-dimethylphenyl)-3,6-dihydro-2H-pyran

HRID 237564ノート

反応式

HRID 237564 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:10].[O:11]1[CH2:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:14]2[CH2:15][CH2:16][O:11][CH2:12][CH:13]=2)=[CH:4][C:3]=1[CH3:10]

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27580472,5-Dibromo-1,3-dimethylbenzeneHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

生成物 1

HCID 866863534-(4-bromo-3,5-dimethylphenyl)-3,6-dihydro-2H-pyran

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

In a microwave vial 2,5-dibromo-1,3-dimethylbenzene (800 mg), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (640 mg) and K3PO4 (1.3 g) are suspended in toluene (12 mL) and water (1.2 mL) and purged for 10 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-(II) (100 mg) is added, the vial is sealed and the mixture is stirred at 60° C. for 12 hours. After cooling to room temperature the mixture is diluted with diethylether and washed with saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40) to give the title compound. Yield: 404 mg.

後処理

  1. customwater (1.2 mL) and purged for 10 minutes with argon
  2. addition[1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-(II) (100 mg) is added
  3. customthe vial is sealed
  4. temperatureAfter cooling to room temperature the mixture
  5. additionis diluted with diethylether
  6. washwashed with saturated aqueous NH4Cl solution
  7. dry with materialThe organic phase is dried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40)

出典と根拠

ORDレコード
ord-82ddc4e4fd2f419fa0d403445ed4b98a
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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