Ethanol → Ethyl 3-(bromophenyl)acetate

HRID 1525325Notes

Reaction equation

HRID 1525325 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH2:19](O)[CH3:20]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:19][CH3:20])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11470552Ethyl 3-(bromophenyl)acetateYield 93%

Procedure

3-Bromophenylacetic acid, 35i-a, (50 g, 0.23 mol) was dissolved in ethanol (250 mL) and sulfuric acid was added drop-wise. The mixture was heated to reflux and stirred overnight. The solution was adjusted to about a pH of 7-8 with sodium hydroxide solution and concentrated in vacuo. The water phase was extracted with ethyl acetate (3×150 mL) and the combined organics was washed with brine (50 mL) and dried, concentrated to give the compound, 35i-b, (52.6 g, 93%) as colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.24-1.29 (m, 3H), 3.58 (s, 2H), 4.11-4.19 (m, 2H), 7.18-7.25 (m, 2H), 7.38-7.44 (m, 2H). LC-MS (M+H)+ 243, 245.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. extractionThe water phase was extracted with ethyl acetate (3×150 mL)
  5. washthe combined organics was washed with brine (50 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c740c95733ad4f98b208c387e792eaf7
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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