Bromine → 2-Amino-5-bromo-3-methoxybenzoic acid

HRID 475315Notes

Reaction equation

HRID 475315 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:13]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 454804572-Amino-5-bromo-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

2-amino-3-methoxybenzoic acid (20.0 g, 119.64 mmol) is suspended in chloroform, cooled to 0° C. and combined with bromine (6.48 mL, 126.56 mmol), which is dissolved in 100 mL chloroform. After the addition the reaction mixture is heated to 20° C. and stirred for 16 h at this temperature. The precipitate is filtered off, dried and 2-amino-5-bromo-3-methoxybenzoic acid (HPLC-MS: tRet.=1.76 min, MS(M+H)+=246/248; method FECS) is obtained.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureis heated to 20° C.
  3. filtrationThe precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-f7a4a251d15a472daac836d30ee15aae
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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