Hydrochloric Acid → 2-tert-Butyl-7-nitro-6-phenyl-1,3-benzoxazole-4-carboxylic Acid

HRID 17516노트

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HRID 17516 반응식
Br[C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]2[O:8][C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:6][C:5]2=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:9]([C:7]1[O:8][C:4]2[C:5](=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=[C:2]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:3]=2[N+:18]([O-:20])=[O:19])[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 685852286-Bromo-2-tert-butyl-7-nitro-1,3-benzoxazole-4-carboxylic Acid

생성물 1

HCID 685849732-tert-Butyl-7-nitro-6-phenyl-1,3-benzoxazole-4-carboxylic Acid수율 140.6%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
85 °C

실험 절차

6-Bromo-2-tert-butyl-7-nitro-1,3-benzoxazole-4-carboxylic acid (I-222) (2.15 g, 6.27 mmol), phenylboronic acid (1.53 g, 12.53 mmol) and aqueous 2 M sodium carbonate solution (20 ml) were suspended in toluene (40 ml) and ethanol (30 ml). Tetrakis(triphenylphosphine)palladium(0) (724 mg, 0.63 mmol) was added at room temperature to the suspension. The mixture was stirred at 85° C. for 22 hours, then cooled to room temperature. The reaction liquid was fractionated with ethyl acetate and aqueous 1 M hydrochloric acid solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was removed by filtration, the solvent was evaporated away and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=9:1) to obtain the entitled compound (3.00 g) as a brown gel. This was used in the next reaction as such.

후처리

  1. temperaturecooled to room temperature
  2. customThe reaction liquid
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was removed by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=9:1)

출처 및 근거

ORD 기록
ord-7bc785322e494398b3aafb9ffc3a2b38
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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