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

HRID 17516ノート

反応式

HRID 17516 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7bc785322e494398b3aafb9ffc3a2b38
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…