Phosphorus tribromide → Methyl 4-bromo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

HRID 595239

反応式

HRID 595239 の反応式
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:3]1.P(Br)(Br)[Br:17]>ClCCl.C(=O)(O)[O-].[Na+]>[Br:17][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 24614Phosphorus tribromideHCID 11275758Methyl 4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate

生成物 1

HCID 118208723Methyl 4-bromo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Methyl 4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate (3.68 g, 17.84 mmol) was taken-up in dichloromethane (17.8 ml) and the solution was purged and then evacuated with argon. Phosphorus tribromide (3.4 ml, 36 mmol) was added, and the resulting mixture was allowed to stir at room temperature over the weekend. The reaction was diluted with aqueous sodium bicarbonate and product was extracted with dichloromethane (3×). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford racemic methyl 4-bromo-1,2,3,4-tetrahydronaphthalene-1-carboxylate as a light yellow oil.

後処理

  1. customthe solution was purged
  2. customevacuated with argon
  3. extractionwas extracted with dichloromethane (3×)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b843e631ab2c4f7f878122d46932855c
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

関連ノート

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