1-(2-Bromoethoxy)-4-chlorobenzene → HCID 1736098, compound

HRID 2389501Notes

Reaction equation

HRID 2389501 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CCN(C(C)C)C(C)C.Br[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][S:1][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 81531DiisopropylethylamineHCID 178527775HCID 178527775, compound

Product 1

HCID 1736098HCID 1736098, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-sulfanylbenzimidazole (159 mg, 1.06 mmol) and DIPEA (150 mg, 200 μl, 1.16 mmol) in dry THF (3 ml) is refluxed for half an hour. After cooling to rt, 1-(2-bromo-ethoxy)-4-chloro-benzene (250 mg, 1.06 mmol) is added. After a further 4 h of reflux, the solvents are removed in vacuo and the residue purified by flash chromatography on silica gel (AcOEt/heptane, 1:9 to 3:7), yielding the title compound (285 mg) in 88% as a white solid: tR=5.40 min (LC-1), ESI-MS (neg.): m/z 303.0 [M−H]+; 1H-NMR (CDCl3): δ 3.76 (t, 2H, SCH2), 4.31 (t, 2H, OCH2), 6.76 (d, 2Harom), 7.18 (d, 2Harom), 7.22-7.32 (m, 3Harom), 7.57 (m, 1Harom).

Workup

  1. temperatureAfter a further 4 h of reflux
  2. customthe solvents are removed in vacuo
  3. customthe residue purified by flash chromatography on silica gel (AcOEt/heptane, 1:9 to 3:7)

Sources & evidence

ORD record
ord-e4f92b1cf8a6407887d3655387958e56
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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