Acetic Acid → Methyl 2-(3-bromo-4-hydroxyphenyl)acetate

HRID 1420840Notes

Reaction equation

HRID 1420840 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.C(O)(=O)C>C(Cl)(Cl)Cl.ClCCl>[Br:1][C:9]1[CH:8]=[C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[OH:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10634081Methyl 2-(3-bromo-4-hydroxyphenyl)acetateYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Bromine (16.59 g, 104 mmol) in chloroform (25 mL) was added dropwise to a stirred, cooled (0° C.) mixture of methyl 4-hydroxyphenylethanoate (17.25 g, 104 mmol) and acetic acid (10 mL) in chloroform (140 mL). The mixture was stirred at 0° C. for 1 h., diluted with dichloromethane (100 mL), washed with water (2×200 mL) and brine (200 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (25.43 g, 100%). 1H NMR (360 MHz, CDCl3) δ7.39 (1 H, d, J 2.0 Hz), 7.12 (1 H, dd, J 8.3, 2.0 Hz), 6.96 (1 H, d, J 8.3 Hz), 5.54 (1 H, br s), 3.70 (3 H, s), and 3.54 (2 H, s).

Workup

  1. temperaturecooled
  2. washwashed with water (2×200 mL) and brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c2b9b3c837449efae3464675db4ccfc
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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