Pyridine → Dimethyl 6-amino-4-bromo-terephthalate

HRID 34142

Reaction equation

HRID 34142 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[Br:22]Br>ClCCl>[NH2:1][C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH2:9][C:10]([Br:22])([C:12]([O:14][CH3:15])=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 68932527Dimethyl 6-amino-4-bromo-terephthalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

10.5 g (50 mmol) dimethyl amino-terephthalate and 8.1 ml (100 mmol) pyridine are dissolved in 175 ml dichloromethane and at −16° C. a solution of 2.7 ml (52.5 mmol) bromine in 25 ml dichloromethane is added dropwise. It is stirred for 4 hours at 0° C. and then heated overnight to ambient temperature. The mixture is added to ice water, washed three times with water and then dried over magnesium sulphate and evaporated down. The crude product is recrystallised from ethanol.

Workup

  1. additionis added dropwise
  2. temperatureheated overnight to ambient temperature
  3. washwashed three times with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down
  6. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-a137e12451464b238fb9096e7c5a5528
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Linked notes

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