Hydrochloric Acid → 3-Bromo-7-methoxy-1-naphthonitrile

HRID 226272Notes

Reaction equation

HRID 226272 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]#[N:16])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:6]=2Br.O.O.[Sn](Cl)Cl.Cl>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:15]#[N:16])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 111986103,8-Dibromo-7-methoxy-1-naphthonitrile

Product 1

HCID 114709973-Bromo-7-methoxy-1-naphthonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To slurry of 3,8-dibromo-7-methoxy-1-naphthonitrile (1.62 kg) and Tin (II) chloride dihydrate (1.24 kg, 5.50 mol) in acetic acid (5 L) is added conc. HCl (37% wt, 2.50 L) through a dropping funnel at 100° C. during a period of 2 h. The mixture is stirred at 100° C. for 4 h. Then, the mixture is cooled to room temperature. The solid is filtered, washed with 1% wt HCl (2×1.00 L), water (1.00 L) and dried to give the title compound as a white solid (524 g, 73%). 1H NMR (CDCl3): δ8.13 (d, 1H, J=1.8 Hz), 7.93 (d, 1H, J=1.9 Hz), 7.72 (d, 1H, J=9.0 Hz),7.41 (d, 1H, J=2.4 Hz), 7.28 (dd, 1H, J=2.4 Hz, 9.0 Hz), 3.99 (s, 3H).

Workup

  1. temperatureThen, the mixture is cooled to room temperature
  2. filtrationThe solid is filtered
  3. washwashed with 1% wt HCl (2×1.00 L), water (1.00 L)
  4. customdried

Sources & evidence

ORD record
ord-00fba5032eaa402a886b3cb3ee82043e
Source dataset
uspto-grants-2009_07
Patent number
US07557237B2

Reaction notes

Loading…