Phosphorus tribromide → Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-

HRID 982112ノート

反応式

HRID 982112 の反応式
[CH2:1]([O:8][C:9]1[C:14]([CH2:15]O)=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>C(OCC)C>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][Br:20])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24614Phosphorus tribromideHCID 927250(2-(Benzyloxy)-3-methoxyphenyl)methanol

生成物 1

HCID 10852231Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-収率 131.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 15.04 g (62 mmol) of 2-benzyloxy-3-hydroxymethyl-1-methoxybenzene, from Step 2, in 140 mL of diethyl ether at 0° C. was added slowly, with stirring, 2.9 mL (31 mmol) of phosphorous tribromide. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to ambient temperature over a 4 h period. The solution phase was decanted and the reaction was quenched with aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 12.48 g (65% yield) of the title compound.

後処理

  1. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  2. customThe solution phase was decanted
  3. customthe reaction was quenched with aqueous sodium bicarbonate solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with diethyl ether
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-10e4ed91b7df455f810d8a3a426ad410
出典データセット
uspto-grants-1991_02
特許番号
US04994486

反応ノート

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