Triethylamine → tert-Butyl (4-bromo-2-methylphenyl)carbamate

HRID 32794

反応式

HRID 32794 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.CCN(CC)CC.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.[NH4+].[Cl-]>O1CCOCC1.O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:17])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:4]([CH3:9])[CH:3]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 114234-Bromo-2-methylanilineHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonate

生成物 1

HCID 2735638tert-Butyl (4-bromo-2-methylphenyl)carbamate収率 79.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r.t., were added Et3N (2.7 mL, 1.2 eq) and BOC2O (4.2 g, 1.2 eq). The reaction mixture was stirred at r.t. for 96 hr. Sat.aq. NH4Cl and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2×20 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH)) to give the title compound as a white solid (1.22 g, 79%).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  4. filtrationthe solids were filtered
  5. customthe solvent evaporated
  6. customThe residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH))

出典と根拠

ORDレコード
ord-fa511c497d154a0b80b25451fc45b008
出典データセット
uspto-grants-2008_09
特許番号
US07427630B2

関連ノート

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