Boron tribromide → HCID 66844842, compound

HRID 253129Notes

Reaction equation

HRID 253129 reaction equation
B(Br)(Br)Br.C1([O:10][C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=2)CCCC1>C(Cl)Cl>[O:10]=[C:11]1[NH:12][CH:13]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:19]=[C:20]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66844763HCID 66844763, compound

Product 1

HCID 66844842HCID 66844842, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron tribromide (1.0 M in CH2Cl2, 10.6 mL, 10.6 mmol) was added to a solution of the nicotinate (Step 1, 1.44 g, 4.81 mmol) in 40 mL of CH2Cl2 at −10° C. The cooling bath was removed and stirring was continued at room temperature for 16 h. The reaction mixture was neutralized with saturated NaHCO3 solution and the resultant tan precipitate was filtered and washed with copious amounts of H2O to give 0.77 g (70%) of the title compound. MS m/z: 231 (M+1).

Workup

  1. customThe cooling bath was removed
  2. filtrationthe resultant tan precipitate was filtered
  3. washwashed with copious amounts of H2O

Sources & evidence

ORD record
ord-3afd2cb903694e98b5fe614eb489bcc2
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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