Hydrochloric Acid → 2-Propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene

HRID 352279ノート

反応式

HRID 352279 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)(=O)=O.[F:22][C:23]1[CH:24]=[C:25](OB(O)O)[CH:26]=[C:27]([F:30])[C:28]=1[F:29].FC1C=C(Br)C=C(F)C=1F.[Mg].COB(OC)OC.Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.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.O>[CH2:17]([CH:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:25]3[CH:24]=[C:23]([F:22])[C:28]([F:29])=[C:27]([F:30])[CH:26]=3)[CH:8]=2)[CH2:13]1)[CH2:18][CH3:19]

参加物

11

反応物 7

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 62657Potassium Phosphate, TribasicHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224MagnesiumHCID 21870694HCID 21870694、化合物HCID 227090452-Propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate

生成物 1

HCID 227090512-Propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene収率 13.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3.8 g of the produced 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate, 3.0 g of 3,4,5-trifluorophenylboric acid (this compound was produced by reacting a Grignard reagent prepared from 3,4,5-trifluorobromobenzene and magnesium, with trimethoxy borane, and then performing a hydrolysis with dilute hydrochloric acid), 0.13 g of tetrakis(triphenylphosphine)palladium(0), and 3.6 g of potassium phosphate in 20 ml of dimethyl formamide (DMF) was stirred for 10 hours at 80° C. The mixture was subsequently cooled to room temperature, 20 ml of water was added, the mixture was extracted with toluene, and the organic layer was washed subsequently with water and then a saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel column chromatography (hexane) and then recrystallized 3 times from ethanol to obtain 0.5 g of 2-propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene.

後処理

  1. customwas produced
  2. temperatureThe mixture was subsequently cooled to room temperature
  3. extractionthe mixture was extracted with toluene
  4. washthe organic layer was washed subsequently with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate
  6. customThe crude product obtained by removal of the solvent by evaporation
  7. customwas purified by silica gel column chromatography (hexane)
  8. customrecrystallized 3 times from ethanol

出典と根拠

ORDレコード
ord-f165dfb7de764579bc3f25abc5a6e8be
出典データセット
uspto-grants-2004_06
特許番号
US06746728B1

反応ノート

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