Boron tribromide → HCID 52912206, compound

HRID 244329Notes

Reaction equation

HRID 244329 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([O:24]C)[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[N:13]=[CH:12][CH:11]=[CH:10]2.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([OH:24])[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[N:13]=[CH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58241681HCID 58241681, compound

Product 1

HCID 52912206HCID 52912206, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −78° C., 1N BBr3 in CH2Cl2 (1.5 ml, 1.5 mmol) was added to 6,8-dimethoxy-7-o-tolylquinoline (0.10 g, 0.36 mmol) in CH2Cl2 (5 ml), and the mixture was warmed to room temperature and stirred for 6 h. The solution was poured into ice-water and neutralized with saturated NaHCO3 solution. The mixture was extracted with ethyl acetate, and the organic phase was dried with Na2SO4. Purification of the residue by HPLC gave 6,8-dihydroxy-7-o-tolylquinoline (7 mg) as a white powder.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried with Na2SO4
  3. customPurification of the residue by HPLC

Sources & evidence

ORD record
ord-dc7efc25592f42b9a9b9b12694f56efc
Source dataset
uspto-grants-2014_02
Patent number
US08658569B2

Reaction notes

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