Methanol → HCID 66751869, compound

HRID 1962883Notes

Reaction equation

HRID 1962883 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16]C)=[C:11]([F:18])[C:10]=2[CH3:19].CO>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([OH:16])=[C:11]([F:18])[C:10]=2[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 66751751HCID 66751751, compound

Product 1

HCID 66751869HCID 66751869, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (80 ml of a 1M solution in CH2Cl2) was slowly added to a solution of 3-bromo-7-fluoro-6-methoxy-8-methyl-quinoline (5.40 g) in CH2Cl2 (300 ml) at 0° C., under an atmosphere of nitrogen. Upon warming to room temperature, the resulting brown mixture was stirred for 24 hrs and then treated with MeOH (100 ml), stirred for 1 hour and then concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate and washed with water, brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure to obtain 3-bromo-7-fluoro-8-methyl-quinolin-6-ol as brown solid (5.01 g) which was used for the next step without any further purification. 1H NMR (DMSO-d6) δ ppm: 10.75 (1H, s); 8.75 (1H, d); 8.52 (1H, d); 7.18 (1H, d); 3.32 (3H, s); 2.56 (3H, d).

Workup

  1. stirringstirred for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude mixture was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate anhydrous
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77063e07d49c4c34936e725eb71bbcd1
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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