Hydrochloric Acid → 3-Bromo-α-methylenebenzenepropanoic acid

HRID 422901Notes

Reaction equation

HRID 422901 reaction equation
[I-].[Br:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][CH:7]([C:13]([O:15]C)=[O:14])[CH2:8][N+](C)(C)C.[OH-].[Na+].Cl>>[Br:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][C:7](=[CH2:8])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23285624HCID 23285624, compound

Product 1

HCID 179568153-Bromo-α-methylenebenzenepropanoic acidYield 85%

Conditions

Temperature
105 °C

Procedure

To a 10 ml round bottom flask containing 2-(3-bromobenzyl)-3-methoxy-N,N,N-trimethyl-3-oxo-1-propanaminium iodide (0.95 g, 2.15 mmol) was added 1 N aqueous NaOH (4.3 ml). The mixture was heated at 105° C. for 2 hours, then cooled to room temperature and acidified with 0.5 N HCl to pH ˜1. The white precipitate was isolated by filtration, washed with water, and air-dried to give 2-(3-bromobenzyl)acrylic acid 0.44 g, 85% yield, HPLC purity: 93.0%.

Workup

  1. temperaturecooled to room temperature
  2. customThe white precipitate was isolated by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-6995f9e9b615456aab270e20d0a18c4f
Source dataset
uspto-grants-2012_01
Patent number
US08101665B2

Reaction notes

Loading…