Toluene → 1-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine

HRID 1039609ノート

反応式

HRID 1039609 の反応式
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][C:4]([O:3][C:2]([F:1])([F:17])[F:18])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)=[CH:21][CH:22]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidineHCID 23676156Sodium t-butoxide

生成物 1

HCID 684830771-[4-(Phenylmethoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine収率 98.4%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 23136663Tri-tert-butylphosphonium Tetraphenylborate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

4-[4-(Trifluoromethoxy)phenoxy]piperidine (2.61 g), benzyl 4-bromophenyl ether (2.63 g), palladium (II) acetate (0.67 mg), Tri-tert-butyl phosphonium tetraphenyl borate (1.57 mg), sodium tert-butoxide (1.06 g) and toluene (13 mL) were placed in a vessel and heated to reflux for 6 hr under Ar. The reaction mixture was then cooled to room temperature and water (100 mL) and ethyl acetate (100 mL) were added. The organic material was taken up in ethyl acetate. The organic layer was washed three times with water (100 mL×3). The organic layer was filtered to remove harz and then the organic layer was condensed under reduced pressure to afford 4.36 g (98.4% yield) of a pale yellow crystal target compound.

後処理

  1. temperatureheated
  2. temperatureto reflux for 6 hr under Ar
  3. washThe organic layer was washed three times with water (100 mL×3)
  4. filtrationThe organic layer was filtered
  5. customto remove harz
  6. customcondensed under reduced pressure

出典と根拠

ORDレコード
ord-eda3b3c11fd94f64a01bdd352d557dd0
出典データセット
uspto-grants-2013_10
特許番号
US08552188B2

反応ノート

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