Boron tribromide → HCID 66879081, compound

HRID 2265893Notes

Reaction equation

HRID 2265893 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32]C)=[C:6]2[C:11]=1[CH:10]([C:12]([OH:14])=[O:13])[N:9]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:8][CH2:7]2.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]2[C:11]=1[CH:10]([C:12]([OH:14])=[O:13])[N:9]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66878999HCID 66878999, compound

Product 1

HCID 66879081HCID 66879081, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.84 g (1.6 mmol) of 8-bromo-2-[4-(4-fluorophenoxy)benzenesulfonyl]-5-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (crude product, 21B) are dissolved in 20 ml of dichloromethane. At 0° C., a solution of 1.19 g (4.7 mmol) of boron tribromide in 10 ml of dichloromethane is added dropwise, and the solution is allowed slowly to reach room temperature. After two hours, it is washed twice with 2 N HCl and once with H2O, dried with MgSO4 and freed of solvent, resulting in 0.61 g of the title compound which can be reacted further without further purification.

Workup

  1. customto reach room temperature
  2. washit is washed twice with 2 N HCl and once with H2O
  3. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-12775c30d20b46e2ba26b86e45ae47e2
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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