Hydrochloric Acid → 2-(2,3-Difluoro-4-trimethylsilylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane

HRID 351354

反応式

HRID 351354 の反応式
[Li]C[CH2:3][CH2:4][CH3:5].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[F:17].[B:18](OC(C)C)([O:23][CH:24](C)C)[O:19][CH:20](C)C.Cl.OCC(C)(CO)C.S([O-])([O-])(=O)=O.[Mg+2]>C(OC)(C)(C)C.O.O1CCCC1>[F:6][C:7]1[C:8]([F:17])=[C:9]([Si:13]([CH3:14])([CH3:16])[CH3:15])[CH:10]=[CH:11][C:12]=1[B:18]1[O:23][CH2:24][C:4]([CH3:3])([CH3:5])[CH2:20][O:19]1

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31344Neopentyl glycolHCID 108993711,2-Difluoro-3-trimethylsilylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 108918462-(2,3-Difluoro-4-trimethylsilylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

625 ml (1 mol) of 1.6 M BuLi are added dropwise at −78° C. to a solution of 169 g (910 mmol) of 1,2-difluoro-3-trimethylsilylbenzene (5) in 1.41 of dry tetrahydrofuran. After 15 minutes, 276 ml (1.2 mol) of triisopropyl borate are added dropwise. The mixture is allowed to warm to room temperature overnight. 200 ml of water, 200 ml of methyl tert-butyl ether and 100 ml of conc. HCl are subsequently added. The organic phase is washed with water (2×100 ml) and sat. NaCl (1×100 ml) and dried using magnesium sulfate, and the solvent is removed under reduced pressure. The oily residue is dissolved in 270 ml of THF, and 94 g (910 mmol) of neopentyl glycol and 455 g of magnesium sulfate are added. After the mixture has been stirred for 1 hour, the solvent is removed under reduced pressure, and petroleum ether (273 ml) is added to the oily residue. Precipitated neopentyl glycol is removed by filtration. 251 g (87%) of 6 crystallise from the filtrate at −25° C.

後処理

  1. washThe organic phase is washed with water (2×100 ml) and sat. NaCl (1×100 ml)
  2. customdried
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe oily residue is dissolved in 270 ml of THF
  5. customthe solvent is removed under reduced pressure, and petroleum ether (273 ml)
  6. additionis added to the oily residue
  7. customPrecipitated neopentyl glycol is removed by filtration
  8. custom251 g (87%) of 6 crystallise from the filtrate at −25° C.

出典と根拠

ORDレコード
ord-5f2aab828df24c91a41d91c180b8bf92
出典データセット
uspto-grants-2007_02
特許番号
US07183447B2

関連ノート

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