10-Bromo-9-fluoro-2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine → 10-Bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 575013노트

반응식

HRID 575013 반응식
[Br:1][C:2]1[C:3]([F:18])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([I:16])=[C:10]3I)[C:6]=2[CH:17]=1.C([Mg]Br)C>O1CCCC1>[Br:1][C:2]1[C:3]([F:18])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([I:16])=[CH:10]3)[C:6]=2[CH:17]=1

참가 물질

4

반응물 2

HCID 8669304910-Bromo-9-fluoro-2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 6831272510-Bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine수율 309.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

Into a 20-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 9-Bromo-8-fluoro-2,3-diiodo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene (886 g, 1.66 mol, 1.00 equiv) in tetrahydrofuran (7 L), followed by the addition of ethylmagnesium bromide (1987 mL, 1.20 equiv, 1 M) dropwise with stirring at −40° C. The resulting solution was stirred at room temperature for 30 min. This reaction was repeated for 2 times. The reaction was then quenched by the addition of 10 L of saturated aqueous NH4Cl and diluted with 24 L of tetrahydrofuran. The resulting solution was separated and the aqueous layer was extracted with 4×3 L of tetrahydrofuran. The organic layers were combined and concentrated under vacuum. The solids were collected by filtration, washed with 1)(2 L of EA and dried to afford 2100 g (crude) of 9-Bromo-8-fluoro-2-iodo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene as a brown solid.

후처리

  1. customInto a 20-L 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred at room temperature for 30 min
  4. customThe reaction was then quenched by the addition of 10 L of saturated aqueous NH4Cl
  5. additiondiluted with 24 L of tetrahydrofuran
  6. customThe resulting solution was separated
  7. extractionthe aqueous layer was extracted with 4×3 L of tetrahydrofuran
  8. concentrationconcentrated under vacuum
  9. filtrationThe solids were collected by filtration
  10. washwashed with 1)(2 L of EA
  11. customdried

출처 및 근거

ORD 기록
ord-c8ff6ca84c75422dab38c490719d5955
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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