1,3-Dibromopropane → Methyl 2-[4-(3-bromopropoxy)phenyl]acetate

HRID 1392284Notes

Reaction equation

HRID 1392284 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH2:15][CH2:14][Br:13])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10803177Methyl 2-[4-(3-bromopropoxy)phenyl]acetateYield 82.1%

Procedure

This compound was produced using similar methods as those used Step 3, example 6, starting with (4-hydroxy-phenyl)-acetic acid methyl ester (5.00 g, 30.1 mmol), 1,3-dibromopropane (24.3 g, 120 mmol) and cesium carbonate (40.3 g, 120 mmol). The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give [4-(3-Bromo-propoxy)-phenyl]-acetic acid methyl ester (7.10 g, 82%) as a faint-yellow oil. 1H NMR (400 MHz, DMSO-d6); δ 7.15 (d, 2H), 6.87 (d, 2H), 4.03 (t, 2H), 3.63 (t, 2H), 3.58 (s, 3H), 3.57 (s, 2H), 2.21 (m, 2H).

Workup

  1. customThis compound was produced
  2. customThe crude oil was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-b51d2b3ee5744fd582c6541869aa9433
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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