Hydrochloric Acid → Methyl 2-(3-bromo-2-hydroxyphenyl)acetate

HRID 1187137Notes

Reaction equation

HRID 1187137 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].C(NC(C)C)(C)C.C1C(=O)N([Br:27])C(=O)C1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:27])[C:6]=1[OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 12159074Methyl 2-(3-bromo-2-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl(2-hydroxyphenyl)acetate (14.0 g, 84.3 mmol) in 100 mL of DCM was added diisopropyl-amine (1.70 g, 16.8 mmol) and NBS (15 g, 84.2 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h. The reaction was poured into 1N HCl, extracted with DCM, and concentrated to give crude methyl(3-bromo-2-hydroxyphenyl)acetate.

Workup

  1. extractionextracted with DCM
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a3de54fbec164a0c989211a5dd9aaa04
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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