Hydrogen Bromide → 8-Bromonaphthalene-2-carboxylic acid

HRID 330508Notes

Reaction equation

N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11]2.[BrH:19]>OS(O)(=O)=O.CC(O)=O.O>[Br:19][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11]2

Participants

Conditions

Temperature: 10 °C

Procedure

According to the procedure of W. Adcock, et al. Aust. J. Chem. 18, 1351 (1965) and H. H. Hodgson, et al. J. Chem. Soc., 1620 (1933), to a cooled (10° C.), stirred solution of NaNO2 (1.24 g, 0.0179 mol) in H2SO4 (16.1 mL) and HOAc (14.9 mL) [prepared by adding NaNO2 to cooled (10° C.) H2SO4, heating to dissolve, recooling, and adding HOAc] was added a solution of 8-amino-2-naphthoic acid (2.80 g, 0.0150 mol) in HOAc (50 mL) over 10 minutes. The resulting solution was added slowly (over 10 minutes) to a heated (60° C.), stirred solution of CuBr (9.44 g, 0.0658 mol) in concentrated HBr (90 mL). The mixture was warmed to 90° C. for 10 minutes, cooled, diluted with H2O (200 mL) and filtered to give a green solid, 3.4 g. The crude product was combined with similarly prepared material (450 mg) and recrystallized from EtOH to give an off-white solid (2.3 g, 55%), m.p. 265°-266° C.

Workup

additionThe resulting solution was added slowly (over 10 minutes) to
temperaturea heated (60° C.)
temperatureThe mixture was warmed to 90° C. for 10 minutes
temperaturecooled
filtrationfiltered
customto give a green solid, 3.4 g
customrecrystallized from EtOH

Sources & evidence

ORD record: ord-98360b34f7ef410d90cba5712cc7bcd2
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897405

Reaction notes

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