Phosphorus tribromide → HCID 22262941, compound

HRID 489726Notes

Reaction equation

HRID 489726 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C:7]([CH2:16]O)=[C:6]1[CH3:18])(=[O:4])=[O:3].P(Br)(Br)[Br:20]>C(OCC)C.O1CCCC1>[Br:20][CH2:16][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]=1[CH3:18]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 22262935HCID 22262935, compound

Product 1

HCID 22262941HCID 22262941, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1-Methanesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-methanol (1.53 g, 5.68 mmol) in anhydrous ethyl ether (50 ml) and tetrahydrofuran (20 ml) at 0° C. under N2 was added a solution of phosphorus tribromide (7.5 ml, 1 M in dichloromethane). The mixture was stirred at room temperature for 8 hours and concentrated under reduced pressure to give 3-bromomethyl-1-methane sulfonyl-5-methoxy-2-methyl-1H-indole as white solid. 1H NMR (CDCl3) δ:2.57 (s, 3H), 3.04(s, 3H), 3.89 (s, 3H), 4.63 (s, 2H), 6.93 (dd, 1H, J=9.1 Hz, 2.5 Hz), 7.04 (d, 1H, J=2.5 Hz), 7.89 (d, 1H, J=9.1 Hz).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0da9e134310c4a52b883a0069a3619db
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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