[1,1'-Biphenyl]-4-carboxylicacid, 4'-bromo-, methyl ester → [4-(4-Bromophenyl)phenyl]methanol

HRID 900358

반응식

HRID 900358 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 737627[1,1'-Biphenyl]-4-carboxylicacid, 4'-bromo-, methyl esterHCID 21226445Aluminium lithium hydride

생성물 1

HCID 1393673[4-(4-Bromophenyl)phenyl]methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 4′-Bromo-biphenyl-4-carboxylic acid methyl ester, 7.8 g (27.9 mmol) in 150 mL of tetrahydrofuran was cooled to 0° C. via ice-water bath. Lithium aluminum hydride, 1.1 g (27.9 mmol) was added to the solution in one portion. The reaction mixture stirred at 0° C. for 1 h. The mixture was slowly quenched with 10 mL of isopropyl alcohol, then with 10 mL of water. The aqueous mixture was extracted with 3×50 mL portions of ethyl acetate. The organic layers were combined, washed with sat. aq. NaCl, and dried (MgSO4). The solution was concentrated to afford the desired product in 7.01 g (100%) as a white solid. The material was taken to the next step without further purification.

후처리

  1. customThe mixture was slowly quenched with 10 mL of isopropyl alcohol
  2. extractionThe aqueous mixture was extracted with 3×50 mL portions of ethyl acetate
  3. washwashed with sat. aq. NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution was concentrated

출처 및 근거

ORD 기록
ord-5bbcda0085a04002b3b2d7badef5ace6
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358248B2

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