Methyl 3-(3,5-dibromo-4-hydroxyphenyl)propionate → 3-[3,5-Dibromo-4-(3-hydroxybenzyloxy)phenyl]propionic acid

HRID 892290Notes

Reaction equation

HRID 892290 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].C([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Br)[CH:21]=1)(=O)C>>[Br:9][C:6]1[CH:5]=[C:4]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:3]=[C:2]([Br:1])[C:7]=1[O:8][CH2:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([OH:19])[CH:21]=1

Participants

3

Reactant 2

HCID 624213Methyl 3-(3,5-dibromo-4-hydroxyphenyl)propionateHCID 64220753-(Bromomethyl)phenyl acetate

Product 1

HCID 222422813-[3,5-Dibromo-4-(3-hydroxybenzyloxy)phenyl]propionic acidYield 78%

Procedure

Methyl 3-(3,5-dibromo-4-hydroxyphenyl)propionate (0.15 g, 0.44 mmol) was coupled with 3-bromomethylphenyl acetate (0.20 g, 0.88 mmol) using the procedure described in Method D4. Purification on column (silica gel, dichloromethane/methanol, gradient elution from 95:5 to 90:10) gave 123 mg (78%) of 3-[3,5-dibromo-4-(3-hydroxybenzyloxy)phenyl]propionic acid. MS: m/z 430.1 (M+−1).

Workup

  1. customPurification
  2. washon column (silica gel, dichloromethane/methanol, gradient elution from 95:5 to 90:10)

Sources & evidence

ORD record
ord-9ad7dd7d3d274059adbe6e110601dd73
Source dataset
uspto-grants-2006_02
Patent number
US07005538B1

Reaction notes

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