Hydrogen Bromide → [2-(Bromomethyl)phenyl]acetic acid

HRID 1831942Notes

Reaction equation

HRID 1831942 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])[O:2]1.[BrH:12]>C(O)(=O)C>[Br:12][CH2:1][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:4][C:3]([OH:2])=[O:11]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 780921,4-dihydro-3H-2-benzopyran-3-one

Product 1

HCID 12889260[2-(Bromomethyl)phenyl]acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of isochroman-3-one (1.5 g, 10 mmol) in 30% HBr in acetic acid (13 mL) was stirred at room temperature for 2 h, and 70° C. for 1 h. The reaction mixture was cooled to room temperature, and poured into ice-water. The precipitate was collected to afford (2-bromomethylphenyl)acetic acid as an off-white solid (2.15 g, 93%): 1H NMR (300 MHz, DMSO-d6) δ 7.45-7.23 (m, 4H), 4.73 (s, 2H), 3.73 (s, 2H).

Workup

  1. customThe precipitate was collected

Sources & evidence

ORD record
ord-e57454d2ab714c6b9439b7652d462af5
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

Loading…