Diiodomethane → 2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 891951

반응식

HRID 891951 반응식
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH2:16])[CH:10]=2)[O:3]1.[CH2:18]([Zn]CC)C.ICI.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH:15]1([C:11]2[CH:10]=[C:9]([B:4]3[O:3][C:2]([CH3:17])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:14]=[CH:13][CH:12]=2)[CH2:18][CH2:16]1

참가 물질

6

반응물 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 222401702-(3-Ethenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 222402222-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane수율 69%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 4,4,5,5-tetramethyl-2-(3-vinyl-phenyl)-[1,3,2]dioxaborolane (300 mg, 1.3 mmol) in toluene (10 ml) were added diethylzinc solution (1.1 N in toluene, 5.22 ml, 5.74 mmol) and diiodomethane (8.7 ml, 33 mmol). The reaction mixture was stirred for 1 hour at room temperature and then refluxed for 3 hours. The reaction mixture was poured on sat. NH4Cl solution (20 ml) and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 2-(3-cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (69% yield), 1H-NMR (300 MHz, CDCl3): δ=7.12-7.82 (m, 4H), 1.35 (s, 12H), 1.28 (t, 1H), 0.90-0.96 (m, 2H), 0.72-0.78 (m, 2H).

후처리

  1. temperaturerefluxed for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-16faa739c8524138aadf0fb8526258e3
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005432B2

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