1,4-Dibromobenzene → 1093878-29-5

HRID 385719노트

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HRID 385719 반응식
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

참가 물질

8

반응물 5

HCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 150242543-OxetanoneHCID 178418306HCID 178418306, 화합물2회

생성물 1

HCID 583822471093878-29-5

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-58b3f69ce2b04318859e0fe1187b966a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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