Methyl chlorodifluoroacetate → 1-Tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene

HRID 74001

반응식

HRID 74001 반응식
[C:1]([C:5]1[CH:10]=[C:9](Br)[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[F-:23].[K+].[K+].[Br-].Cl[C:28]([F:34])([F:33])C(OC)=O>O.[Cu]I.CN(C=O)C>[C:1]([C:5]1[CH:10]=[C:9]([C:28]([F:34])([F:23])[F:33])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 73935Methyl chlorodifluoroacetateHCID 253877Potassium BromideHCID 522689Potassium FluorideHCID 574702371-Tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene

생성물 1

HCID 574702381-Tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene수율 67%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
125 °C

실험 절차

A mixture of 1-tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene (913 mg, 2.5 mmol), KF (291 mg, 5 mmol), KBr (595 mg, 5 mmol), CuI (570 mg, 3 mmol), methyl chlorodifluoroacetate (1.6 mL, 15 mmol) and DMF (5 mL) was stirred at 125° C. in a sealed tube overnight, cooled to room temperature, diluted with water and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by column chromatography (0-5% EtOAc-Hexane) to yield 1-tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene (591 mg, 67%). 1H NMR (400 MHz, CDCl3) 7.66 (s, 1H), 7.37 (m, 5H), 7.19 (s, 1H), 5.21 (s, 2H), 1.32 (s, 9H).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customAfter removal of the solvent
  6. customthe residue was purified by column chromatography (0-5% EtOAc-Hexane)

출처 및 근거

ORD 기록
ord-0e2a8034158147ecb0e8840e9ae30b7d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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