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

HRID 79658ノート

反応式

HRID 79658 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-78f9fb7e10ad45f48877ae2c069d0ecf
出典データセット
uspto-grants-2014_09
特許番号
US08841278B2

反応ノート

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