Trifluoroacetic acid → 2-Bromo-5-methoxy-3-methyl-phenylamine

HRID 2216122Notes

Reaction equation

HRID 2216122 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH3:16])[C:9]=1[Br:17])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:17][C:9]1[C:10]([CH3:16])=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69586528(2-Bromo-5-methoxy-3-methyl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 218864892-Bromo-5-methoxy-3-methyl-phenylamineYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-bromo-5-methoxy-3-methyl-phenyl)-carbamic acid tert-butyl ester ((Example 198: step b) 3.00 g, 9.49 mmol) in CH2Cl2 (50 mL) was treated with trifluoroacetic acid (7.00 mL) dropwise. The solution was stirred at room temperature 1.3 h. The solvents were evaporated in vacuo to yield the product 2-bromo-5-methoxy-3-methyl-phenylamine (2.04 g, 65%) as a yellow solid trifluoroacetate salt. The crude mixture was used directly in the next reaction.

Workup

  1. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-7b7d946aeac9446c9cbf28f5445aa882
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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