Bromine → HCID 53995508, compound

HRID 2187457Notes

Reaction equation

HRID 2187457 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH2:4]1.C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C>[NH2:2][C@@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([Br:20])[CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH2:4]1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 12280574HCID 12280574, compound

Product 1

HCID 53995508HCID 53995508, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R)-2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene hydrochloride (5.0 g, 23 mmol) was dissolved in acetic acid (300 mL) under nitrogen atmosphere. Sodium acetate (5.5 g, 70 mmol) was added and bromine (3.5 g, 23 mmol) was then added in one portion. The mixture was stirred for 5 minutes at room temperature. The solvent was removed in vacuo to give a solid residue which was partitioned between ethyl acetate and NaOH (2 M). The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined and dried (Na2SO4). The solvent was removed in vacuo to give a brown oily residue. The HCl salt was precipitated from diethyl etherimethylene chloride by the addition of HCl in diethyl ether (3 M): yield 7.7 g (94%). Recrystallization from methanol gave the title compound as needle crystals: mp 264-265° C.; [α]21D +54° (c 1, MeOH); EIMS (70 eV) m/z (relative intensity) 257 (30, M+, 81Br), 255 (31, M+, 79Br).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a solid residue which
  3. customwas partitioned between ethyl acetate and NaOH (2 M)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customto give a brown oily residue
  9. customThe HCl salt was precipitated from diethyl etherimethylene chloride by the addition of HCl in diethyl ether (3 M)
  10. customRecrystallization from methanol

Sources & evidence

ORD record
ord-745a7183c9ad4c0f8910036442df9786
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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