Hydrochloric Acid → 2-(3,4-Difluorophenyl)-6-(4-propylphenyl)-1,2,3,4-tetrahydronaphthalene

HRID 352283

반응식

HRID 352283 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Mg].COB(OC)OC.Cl.Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][CH:26]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[C:33]([F:38])[CH:32]=1)[CH2:25][CH2:24]2.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>[F:38][C:33]1[CH:32]=[C:31]([CH:26]2[CH2:25][CH2:24][C:23]3[C:28](=[CH:29][CH:30]=[C:21]([C:7]4[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=4)[CH:22]=3)[CH2:27]2)[CH:36]=[CH:35][C:34]=1[F:37]

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 62657Potassium Phosphate, TribasicHCID 1363741-Bromo-4-propylbenzeneHCID 5462224MagnesiumHCID 22709043HCID 22709043, 화합물

생성물 1

HCID 227090532-(3,4-Difluorophenyl)-6-(4-propylphenyl)-1,2,3,4-tetrahydronaphthalene

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A solution of 4.5 g of 4-propylphenylboric acid obtained by reaction of a Grignard reagent prepared from 4-propylbromobenzene and magnesium with trimethoxy borane and subsequent hydrolysis with dilute hydrochloric acid, 5.0 g of 6-bromo-2-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalene synthesized in the example 15, 0.3 g of tetrakis(triphenylphosphine)palladium(0), and 3.0 g of potassium phosphate in 30 ml of dimethyl formamide was stirred for 10 hours at 80° C. The mixture was subsequently cooled to room temperature, water was added, and the mixture was extracted with toluene. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (hexane) and then recrystallized from ethanol, and yielded 4 g of 2-(3,4-difluorophenyl)-6-(4-propylphenyl)-1,2,3,4-tetrahydronaphthalene. This compound displayed a purity of 99.7% when analyzed by gas chromatography, and had a molecular weight of 362.

후처리

  1. temperatureThe mixture was subsequently cooled to room temperature
  2. extractionthe mixture was extracted with toluene
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane)
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-ae4514c24a244888b6d3cb4fd123196c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06746728B1

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