Sodium Carbonate → tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 564048Notes

Reaction equation

HRID 564048 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.[C:13]([O-:16])([O-])=[O:14].[Na+].[Na+]>C(Cl)Cl.O>[C:6]([O:16][C:13]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([Br:2])=[CH:4][CH:5]=2)[CH2:10]1)=[O:14])([CH3:11])([CH3:7])[CH3:5]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 450739697-Bromo-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 15885175tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 10.0 g (40.2 mmol) 7-bromo-1,2,3,4-tetrahydro-isoquinoline hydrochloride in 250 mL DCM and 50 mL (101 mmol) 2M aqueous Na2CO3-solution is added a solution of 9.27 g (42.5 mmol) BOC-anhydride in DCM. The reaction is stirred 1 h at RT and is diluted with 100 mL water. The organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. To the residue is added PE and the mixture is cooled to −30° C. The precipitate is collected, washed with cold PE and dried.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. additionTo the residue is added PE
  6. temperaturethe mixture is cooled to −30° C
  7. customThe precipitate is collected
  8. washwashed with cold PE
  9. customdried

Sources & evidence

ORD record
ord-5c63a1a17cf34099bc73404f71cdeb51
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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