Water → 4'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrile

HRID 494850ノート

反応式

HRID 494850 の反応式
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 962Water2 回HCID 25134Boron tribromideHCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

生成物 1

HCID 136359914'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrile収率 94.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The product from Example 106A (5.60 g, 25.4 mmol) in CH2Cl2 (120 mL) at 78° C. was treated with 1.0 M BBr3 (in CH2Cl2, 76 mL, 76.0 mmol) dropwise over 1 hour. After stirring for 14 hours at room temperature, the mixture was warmed to 0° C. (ice bath) and treated with water (0.5 mL). After 10 minutes, additional water was added (2.0 mL), ice bath was removed, and 5.0 mL of water was added. The mixture was then treated with another 20 mL of water and allowed to stir for 45 minutes. The mixture was filtered and the filtrate extracted with CH2Cl2. The CH2Cl2 layers were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as an off-white powder (5.04 g, 94% yield). 1HNMR (300 MHz, CDCl3) δ 2.35 (s, 3H), 5.0 (s, 1H), 6.79-7.50 (m, 7H); MS (DCI) m/z 210 (+H)+.

後処理

  1. temperaturethe mixture was warmed to 0° C. (ice bath)
  2. waitAfter 10 minutes
  3. customwas removed
  4. addition5.0 mL of water was added
  5. additionThe mixture was then treated with another 20 mL of water
  6. stirringto stir for 45 minutes
  7. filtrationThe mixture was filtered
  8. extractionthe filtrate extracted with CH2Cl2
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-bd88652c3e4d49dfbbfe42c5316495bd
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

反応ノート

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