Hydrochloric Acid → 2-Naphthol, 1,6-dibromo-

HRID 1035590Notes

Reaction equation

HRID 1035590 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C1C(=O)N([Br:20])C(=O)C1.Cl.C(OCC)(=O)C>CC(C)=O>[Br:20][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 271446-Bromo-2-naphthalenolHCID 67184N-bromobutanimide

Product 1

HCID 277682-Naphthol, 1,6-dibromo-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Bromo-2-naphthol (500 mg, 2.242 mmol, 1 eq) and NBS (558.7 mg, 3.319 mmol, 1.4 eq) are stirred at RT in 4.4 ml of acetone and 22 μl of 1 N HCl for 15 min. Ethyl acetate is added, and this organic phase is washed three times with 1 N HCl. After drying over magnesium sulfate, filtering and concentrating in vacuum on a rotary evaporator, the desired product is obtained in quantitative yield (677 mg).

Workup

  1. washthis organic phase is washed three times with 1 N HCl
  2. dry with materialAfter drying over magnesium sulfate
  3. filtrationfiltering
  4. concentrationconcentrating in vacuum on a rotary evaporator

Sources & evidence

ORD record
ord-b68191a7d1f54bb5a505f482983b8aca
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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