Hydrochloric Acid → 3,5-Diiodo-4-(3-bromobenzyloxy)benzoic Acid

HRID 1839903Notes

Reaction equation

HRID 1839903 reaction equation
[OH-].[Li+].BrC1C=C(C=CC=1)C[O:8][C:9](=[O:27])[C:10]1[CH:15]=[C:14]([I:16])[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=2)=[C:12]([I:26])[CH:11]=1.Cl>C1COCC1>[I:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([I:26])[C:13]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=1)[C:9]([OH:27])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 121488754-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl Ester

Product 1

HCID 99376563,5-Diiodo-4-(3-bromobenzyloxy)benzoic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of lithium hydroxide (0.5 mL, 0.6 mmol) was added to a solution of 4-(3-bromo-benzyloxy)-3,5-diiodo- benzoic acid 3-bromo-benzyl ester (as prepared in Example 1, 363 mg, 0.5 mmol) in 4 mL THF. The biphasic solution was stirred for 17 hours, after which time the reaction mixture was poured into 1 M HCl (15 mL). The resulting white precipitate was isolated by filtration, rinsed with water, and dried in vacuo, yielding the title compound as a white powder (270 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 13.39 (br. s, 1H), 8.33 (s, 2H), 7.81 (s, 1H), 7.63-7.61 (m, 2H), 7.44 (appar. t, J=7.8 Hz, 1H), 5.00 (s, 2H). HPLC (30-90), 17.20 min. LRMS (EI−) calc'd for [C14H9BrI2O3—H] 556.8, found 556.6.

Workup

  1. customThe resulting white precipitate was isolated by filtration
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-56e6ab1a8c1f4a34b3c1c66e58aaba3c
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

Loading…