Boron tribromide → HCID 71185821, compound

HRID 1470512Notes

Reaction equation

HRID 1470512 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:9][CH:8]=[C:7]2[O:17]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[CH:9][CH:8]=[C:7]2[OH:17]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71186206HCID 71186206, compound

Product 1

HCID 71185821HCID 71185821, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-chloro-4-methoxy-N,N-dimethyl-1-naphthamide (step-5 intermediate) (0.5 g, 1.90 mmol) in DCM (15 mL) was cooled to −78° C. Then, BBr3 (0.72 mL, 7.58 mmol) in DCM (7.5 mL) was added dropwise to the mixture at −78° C. The reaction mixture was warmed to RT and stirred for 2 h, and quenched with brine solution. The aqueous layer was extracted with DCM, and the combined organic layer was washed with, water, brine, dried over Na2SO4 and filtered. The solvent was evaporated to provide the desired phenol as pale brown solid (445 mg, 94%) that was used in next step without any further purification.

Workup

  1. customquenched with brine solution
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organic layer was washed with, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-dd344b96f65a42fd983069e3d32c16d1
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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