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Methyl iodide → 2-[(Methylsulfanyl)methyl]-1,1'-biphenyl

HRID 1013148
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HRID 1013148 반응식
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][SH:8].[CH3:15]I>CO.C[O-].[Na+]>[CH3:15][S:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 21610890HCID 21610890, 화합물

생성물 1

HCID 230891202-[(Methylsulfanyl)methyl]-1,1'-biphenyl수율 77%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 10942334Sodium Methoxide용매

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온도
60 °C

실험 절차

A mixture of biphenyl-2-yl-methanethiol (4 g, 20 mmol) in methanol (27 mL) and sodium methoxide in methanol (0.5 M, 40 mL) was heated at 60° C. for 0.5 h, cooled, treated with methyl iodide (3.7 mL, 60 mmol) and re-heated at 60° C. for 0.5 h. After cooling to room temperature, the reaction mixture was quenched with ice-water, acidified (pH˜2) and extracted with ethyl acetate (3×50 mL). Combined organic layer was washed with water (1×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated to give a crude product that was passed through a bed of silica (solvent: ethyl acetate) to give 3.3 g of 2-methylsulfanylmethyl-biphenyl (yellow oil) that was directly used in the next step.

후처리

  1. temperaturecooled
  2. temperaturere-heated at 60° C. for 0.5 h
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was quenched with ice-water
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washCombined organic layer was washed with water (1×50 mL) and brine (1×50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give a crude product that

출처 및 근거

ORD 기록
ord-e3aa70915ad8463ebf2b18ee2138c9e0
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981907B2

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