Carbon tetrabromide → Methyl 3-(bromomethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

HRID 899452Notes

Reaction equation

HRID 899452 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57775670Methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

Product 1

HCID 59211887Methyl 3-(bromomethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate (2.99 g, 9.92 mmol) in dichloromethane (90 mL) were added carbon tetrabromide (4.28 g, 12.9 mmol) and triphenylphosphine (3.12 g, 11.9 mmol). After 15 h, the reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-40% EtOAc/hexanes) to provide methyl 3-(bromomethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.91 (s, 1H), 7.61 (s, 1H), 4.50 (s, 2H), 3.94 (s, 3H), 3.67 (t, J=7.2 Hz, 2H), 2.90 (s, 3H), 1.56-1.46 (m, 2H), 0.92 (t, J=7.3 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2bcb1fb08e7140a682355a1565223ba1
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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