Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 1501189Notes

Reaction equation

HRID 1501189 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:16])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 94%

Procedure

To a solution of 2-(4-bromophenyl)acetic acid (10 g, 47 mmol) in methanol (100 mL) was dropwise thionyl chloride (0.2 mL) at room temperature. The mixture solution was heated to reflux for 3 hours. Then removed the solvent to dry to gave methyl 2-(4-bromophenyl)acetate as a colorless oil (10 g, 94%). 1H NMR (300 MHz, CDCl3): δ 7.45 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 3.70 (s, 3H), 3.58 (s, 2H).

Workup

  1. customat room temperature
  2. temperatureThe mixture solution was heated
  3. temperatureto reflux for 3 hours
  4. customThen removed the solvent
  5. customto dry

Sources & evidence

ORD record
ord-8c231834565941cf81ab22480cbd3bcd
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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