Triethylamine → 4-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroaniline

HRID 576068ノート

反応式

HRID 576068 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH2:10]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:11]=[CH2:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:13]1([CH2:10]/[CH:11]=[CH:12]/[C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 75027AllylcyclohexaneHCID 80271Tri-o-tolylphosphineHCID 1230504-Bromo-2-fluoroaniline

生成物 1

HCID 867072764-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroaniline収率 69%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Toluene (5 mL) was added to 4-bromo-2-fluoroaniline (950 mg, 5.00 mmol), allylcyclohexane (1.15 mL, 7.50 mmol), palladium acetate (112 mg, 0.50 mmol), tris(2-methylphenyl)phosphine (457 mg, 1.50 mmol) and triethylamine (2.09 mL, 15.0 mmol), and the mixture was stirred, followed by heating to reflux for 10 hr. After cooling, ethyl acetate was added thereto, the mixture was filtered through Celite (registered trademark), and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (805 mg).

後処理

  1. temperatureby heating
  2. temperatureto reflux for 10 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite (registered trademark)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

出典と根拠

ORDレコード
ord-3b399ca8f6234bd1a544d2fcf1048114
出典データセット
uspto-grants-2015_05
特許番号
US09035059B2

反応ノート

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