4-(3-Bromopropoxy)1-phenoxybenzene → 2-Phenoxy-3-[4-(4-phenoxy phenoxy)propoxyphenyl]propanoic acid methyl ester

HRID 459263Notes

Reaction equation

HRID 459263 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 112552434-(3-Bromopropoxy)1-phenoxybenzeneHCID 178401663-(4-Hydroxyphenyl)-2-phenoxypropanoic acid methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 588227012-Phenoxy-3-[4-(4-phenoxy phenoxy)propoxyphenyl]propanoic acid methyl esterYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-hydroxyphenyl)-2-phenoxypropanoic acid methyl ester (0.055 g, 0.18 mmol) with 1-(3-bromopropoxy)-4-phenoxybenzene (Step A) (0.055 g, 0.18 mmol) and potassium tert-butoxide (0.020 g, 0.18 mmol) were stirred in DMF (5 mL) overnight. The mixture reaction concentrated in vacuo with toluene (2 times), reconstituted in Ethyl acetate and washed with water (3 times) and brine, dryed (Na2SO4) and concentrated to afford a crude product that was purified by chromatographied in silicagel (hexanes/Ethyl acetate, 3:1) to give 0.022 g of the title compound (23%). 1H-NMR (200.15 MHz, CDCl3): δ 7.34–7.15 (m, 6H), 7.07–6.71 (m, 12H), 4.80–4.68 (m, 1H), 4.13 (t, 4H, J=15.1), 3.71 (s, 3H), 3.20–3.15 (m, 2H), 2.30–2.18 (q, 2H).

Workup

  1. customThe mixture reaction
  2. concentrationconcentrated in vacuo with toluene (2 times)
  3. washwashed with water (3 times) and brine
  4. concentrationconcentrated
  5. customto afford a crude product that
  6. customwas purified by chromatographied in silicagel (hexanes/Ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-0883f4e3c05b407eb8a759d46c2b5665
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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