Sodium borohydride → 4,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl

HRID 417412노트

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HRID 417412 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[O:18])[C:5]([C:8]2[C:9]([CH:15]=[O:16])=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[CH2:15][OH:16])=[C:4]([CH2:17][OH:18])[CH:3]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 113260944,4'-Dibromobiphenyl-2,2'-dicarbaldehyde

생성물 1

HCID 113721754,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl수율 87%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

The solution of 2,7-dibromo-phenanthrene (3.8 g) in DCM/MeOH (120 ml/1 ml) was cooled to −78° C., and it became a suspension. Ozone was bubbled thorough for 20 minutes, and the mixture became blue. Oxygen was bubbled for 5 minutes and dimethyl sulfide (3 ml) was added. The mixture was warmed to 25° C. and stirred for 12 hours. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave 4,4′-dibromo-biphenyl-2,2′-dicarbaldehyde (600 mg). To the solution of 4,4′-dibromo-biphenyl-2,2′-dicarbaldehyde (600 mg, 1.7 mmol) in THF/MeOH (10 ml/10 ml) at 0° C. was added sodium borohydride (320 mg, 8.2 mmol). The mixture was warmed to 25° C. and stirred for 12 hours. The mixture was quenched with water, and extracted with EtOAc. The organic phase was washed with water and brine, and was dried with sodium sulfate. Concentration gave (4,4′-dibromo-2′-hydroxymethyl-biphenyl-2-yl)-methanol (550 mg).

후처리

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

출처 및 근거

ORD 기록
ord-1092418c2a5041828e6f0e1894dc6442
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088368B2

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