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

HRID 539341
ノート
印刷プレビュー

反応式

HRID 539341 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-9c4b72d9844947228a12072e339521f2
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08865911B2

反応ノート

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