1,4-Dibromobenzene → 1093878-29-5

HRID 385719ノート

反応式

HRID 385719 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C(O[B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)(C)C.[Li]C(C)(C)C.[O:27]1[CH2:30][C:29](=[O:31])[CH2:28]1.[NH4+].[Cl-]>C1COCC1.O>[CH3:19][C:16]1([CH3:18])[C:15]([CH3:20])([CH3:21])[O:14][B:13]([C:2]2[CH:7]=[CH:6][C:5]([C:29]3([OH:31])[CH2:30][O:27][CH2:28]3)=[CH:4][CH:3]=2)[O:17]1

参加物

8

反応物 5

HCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 150242543-OxetanoneHCID 178418306HCID 178418306、化合物2 回

生成物 1

HCID 583822471093878-29-5

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

1,4-Dibromobenzene (3.3 g, 13.99 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.91 mL, 14.27 mmol) were taken up in THF (60 mL) and cooled to −78° C. before adding t-BuLi (16.46 mL, 28.0 mmol) dropwise. After stirring at −78° C. for 40 minutes, additional t-BuLi (16.46 mL, 28.0 mmol) was added. After 30 minutes oxetan-3-one (1.01 g, 13.99 mmol) was added and the reaction mixture was allowed to room temperature over 90 minutes. Water was added followed by saturated NH4Cl and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a white solid.

後処理

  1. waitthe reaction mixture was allowed to room temperature over 90 minutes
  2. extractionthe products were extracted into EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-58b3f69ce2b04318859e0fe1187b966a
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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