Dibah → (2-Bromo-4-fluorobenzo[d]thiazol-6-yl)methanol

HRID 1671784노트

반응식

HRID 1671784 반응식
[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[C:7]([F:15])[C:5]=2[N:6]=1.CC(C[Al]CC(C)C)C>C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]([F:15])[C:5]=2[N:6]=1

참가 물질

5

반응물 2

HCID 16682954DibahHCID 57527206HCID 57527206, 화합물

생성물 1

HCID 57527173(2-Bromo-4-fluorobenzo[d]thiazol-6-yl)methanol수율 89.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate (0.335 g, 1.15 mmol) in toluene (10 mL) and THF (5 mL) was added Dibal-H (4.8 mL, 4.8 mmol) at −78° C. over 10 min. The resulting mixture was allowed to warm to rt and stirred at rt for 3 hr before it was poured into ice cold water (100 mL). The mixture was stirred at rt for 30 min and then filtered through Celite® 545. The organic layer was separated and the aqueous layer was extracted twice with AcOEt. The combined organic phase was dried over anhydrous MgSO4 and concentrated under vacuum. Evaporation of solvent under vacuum gave the title compound (0.269 g, 89% yield) as a white solid.

후처리

  1. stirringThe mixture was stirred at rt for 30 min
  2. filtrationfiltered through Celite® 545
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  6. concentrationconcentrated under vacuum
  7. customEvaporation of solvent under vacuum

출처 및 근거

ORD 기록
ord-3b4e067691c24877be1b550579f1a7e2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994337B2

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