Boron tribromide → 5-Hexyl-2-phenoxyphenol

HRID 2246761노트

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HRID 2246761 반응식
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([O:20]C)[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].ClC1C=CC(OC2C=CC=CC=2)=C(OC)C=1.B(Br)(Br)Br>ClCCl>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([OH:20])[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

5

반응물 3

HCID 25134Boron tribromide2회HCID 586041314-Chloro-2-methoxy-1-phenoxybenzeneHCID 684255854-Hexyl-2-methoxy-1-phenoxybenzene

생성물 1

HCID 52749775-Hexyl-2-phenoxyphenol

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-70 °C

실험 절차

Compound (4a), 1.4 mmol, was dissolved in 3 mL of anhydrous dichloromethane under nitrogen. The temperature of the solution was lowered to −70° C. To the solution of (3) was added 455 mg (1.8 mmol) of boron tribromide (1.8 mL of a 1.0M boron tribromide in dichloromethane solution). The reaction mixture was stirred at −70° C. for one hour, followed by stirring at room temperature for three hours. The reaction progress was monitored by thin layer chromatography. The solution was then quenched with methanol at −70° C. and concentrated. A suspension of the concentrate was washed with 10% aqueous sodium bicarbonate solution. The organic phase was removed, washed with water and then brine (NaCl), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to give the crude product. Purification by flash chromatography on silica gel afforded the analytically pure product (5a): 1H NMR (300 MHz) (CDCl3): δ 7.44-6.76 (m, 8H), 5.58 (s, 1H), 2.66-2.61 (t, 2H), 1.71-1.66 (m, 2H), 1.40-1.34 (m, 6H), 1.00-0.95 (t, 3H).

후처리

  1. customwas lowered to −70° C
  2. stirringby stirring at room temperature for three hours
  3. customThe solution was then quenched with methanol at −70° C.
  4. concentrationconcentrated
  5. additionA suspension of the concentrate
  6. washwas washed with 10% aqueous sodium bicarbonate solution
  7. customThe organic phase was removed
  8. washwashed with water
  9. dry with materialbrine (NaCl), dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customto give the crude product
  13. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-356d5982c9c74312ae73529e81802e32
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687547B2

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