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

HRID 595239Notes

Reaction equation

HRID 595239 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b843e631ab2c4f7f878122d46932855c
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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