1,3-Dibromopropane → 4-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

HRID 29675Notes

Reaction equation

HRID 29675 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.[Br:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:29][CH2:28][CH2:27][Br:26])=[CH:6][C:5]=1[NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:21])[F:23])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 692054424-Hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

Product 1

HCID 692101914-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was produced using similar methods as those used in Step 4, example 27, starting with 4-hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 4.19 mmol), 1,3-dibromopropane (3.39 g, 16.8 mmol) and potassium carbonate (2.90 g, 21.0 mmol) in acetone (85 mL). The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 12/88) to give 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 75%) as a white powder. 1H NMR (400 MHz, CDCl3); δ 12.30 (s, 1H), 8.57 (d, 1H), 8.10 (d, 2H), 8.02 (d, 1H), 7.36 (d, 2H), 6.65 (dd, 1H), 4.24 (t, 2H), 3.93 (s, 3H), 3.61 (t, 2H), 2.35 (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-4af01f20e1a84ee5abd19055cf6feefa
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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