Boron tribromide → HCID 9819159, compound

HRID 397102Notes

Reaction equation

HRID 397102 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([N:5]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[C:12]2[C:7](=[CH:8][C:9]([O:23]C)=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[F:26][C:2]([F:1])([F:25])[C:3]([N:5]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:12]2[C:7](=[CH:8][C:9]([OH:23])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18172443HCID 18172443, compound

Product 1

HCID 9819159HCID 9819159, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2,2-trifluoro-1-[7-methoxy-4-(4-methoxy-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone (1.74 g, 4.76 mmol, see Example 82) in CH2Cl2 (100 ml) cooled to 0° C. was added BBr3 as a 1.0 M solution in CH2Cl2 (14.28 ml, 14.28 mmol) in a dropwise manner. The reaction mixture was stirred at 0° C. for 60 minutes, the ice bath removed, and stirring continued at RT for 90 minutes. MeOH (10 ml) was added to the reaction and stirring was continued at RT for 10 minutes. The reaction mixture was concentrated in vacuo and purified by flash chromatography (Biotage, SiO2, 25-40% EtOAc/hexanes) to give the title product (1.36 g, 4.03 mmol, 85% yield).

Workup

  1. customthe ice bath removed
  2. stirringstirring
  3. waitcontinued at RT for 90 minutes
  4. additionMeOH (10 ml) was added to the reaction
  5. stirringstirring
  6. waitwas continued at RT for 10 minutes
  7. concentrationThe reaction mixture was concentrated in vacuo
  8. custompurified by flash chromatography (Biotage, SiO2, 25-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-46b5e8613b0f48bd89f7a1ea669aec85
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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