Phosphorus tribromide → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl bromide

HRID 1170987노트

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HRID 1170987 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5]O.P(Br)(Br)[Br:24]>COCCOC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5][Br:24]

참가 물질

4

반응물 2

HCID 24614Phosphorus tribromideHCID 251506013,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl alcohol

생성물 1

HCID 251495073,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl bromide수율 82.6%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

To a stirred solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl alcohol (1.0 g, 3.4 mmol) in DME (10 mL) at 0° C. was added phosphorous tribromide (1.8 g, 0.5 mL, 6.8 mmol). The reaction mixture was stirred at 0° C. for 5 h, quenched with methanol (2 mL) and stirred for 30 min. The reaction mixture was poured into ice water and extracted with ether (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl bromide as an oil (1.02 g, 82%): 1H NMR (300 MHz, CDCl3): δ 7.15 (s, 2 H), 6.81 (d, J=3.0 Hz, 1 H), 6.67 (d, J=9.0 Hz, 1 H), 6.34 (dd, J=3.0, 8.7 Hz, 1 H), 4.51 (s, 2 H), 3.80 (s, 3 H), 3.40-3.25 (m, 1 H), 2.15 (s, 6 H), 1.20 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (2:4); Rf=0.7.

후처리

  1. customquenched with methanol (2 mL)
  2. stirringstirred for 30 min
  3. additionThe reaction mixture was poured into ice water
  4. extractionextracted with ether (100 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f14cc5eb32a74a5a8dcdc36656ac730f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829552B2

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