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

HRID 595239노트

반응식

HRID 595239 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b843e631ab2c4f7f878122d46932855c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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