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

HRID 1170987ノート

反応式

HRID 1170987 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f14cc5eb32a74a5a8dcdc36656ac730f
出典データセット
uspto-grants-2010_11
特許番号
US07829552B2

反応ノート

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