Benzyl mercaptan → Benzyl(3-bromo-2-methylphenyl)sulfane

HRID 389677

反応式

HRID 389677 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:61]1([CH2:67][SH:68])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:67]([S:68][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

参加物

7

反応物 4

HCID 7509Benzyl mercaptanHCID 346812,6-DibromotolueneHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

生成物 1

HCID 66911186Benzyl(3-bromo-2-methylphenyl)sulfane

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography.

後処理

  1. customThe reaction was quenched by the addition of 150 ml of H2O
  2. extractionAfter extraction (three times) with ethyl acetate
  3. washthe combined organic layers were washed with water
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customthe product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-fd0db779b5694582a9c0f17d04f568c4
出典データセット
uspto-grants-2013_02
特許番号
US08378092B2

関連ノート

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