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

HRID 1064746

반응식

HRID 1064746 반응식
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

참가 물질

5

반응물 3

HCID 962Water2회HCID 25134Boron tribromideHCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 (M+H)+.

후처리

  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

출처 및 근거

ORD 기록
ord-74aebf7432a44d20ac034b3d7391bcc7
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969730B2

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