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Hydrochloric Acid → 6'-bromo-4,4-difluorospiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 539341
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HRID 539341 반응식
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]1([CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]1)[C:6]2=[N:19]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][C:7]3([CH2:12][CH2:13][C:14]([F:17])([F:18])[CH2:15][CH2:16]3)[C:6]2=[NH:19])=[CH:10][CH:11]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979525N-(5'-Bromo-4,4-difluorospiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

생성물 1

HCID 679795136'-bromo-4,4-difluorospiro[cyclohexane-1,2'-inden]-1'(3'H)-imine수율 99%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

HCl (4M in 1,4-dioxane, 3.38 mL, 13.51 mmol) was added to a solution of N-(5′-bromo-4,4-difluorospiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 27 Step 1, 565 mg, 1.35 mmol) in anhydrous 1,4-dioxane (4 mL). The resulting mixture was stirred under a nitrogen atmosphere at r.t. for 90 min. Et2O (2 mL) was added and the precipitate was filtered off and washed with Et2O. The solid was partitioned between DCM (8 mL) and sat. aq. NaHCO3 (8 mL). The phases were separated and the organic layer was dried over MgSO4 and concentrated to give 6′-bromo-4,4-difluorospiro[cyclohexane-1,2′-inden]-1′(3′H)-imine (418 mg, 99% yield), that was used directly in the next step. MS (ES+) m/z 314 [M+H]+.

후처리

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. customThe solid was partitioned between DCM (8 mL) and sat. aq. NaHCO3 (8 mL)
  4. customThe phases were separated
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9c4b72d9844947228a12072e339521f2
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865911B2

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