Carbon tetrabromide → 1,3-Bis-bromomethyl-5-methoxy-benzene

HRID 1695301Notes

Reaction equation

[C:1]([Br:5])(Br)(Br)Br.[Br:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10](CO)[CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH2:1][Br:5])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Carbon tetrabromide (663 mg) was added to a stirred solution of 1-bromomethyl-3-hydroxymethyl-5-methoxy-benzene (420 mg) in anhydrous dichloromethane (10 mL) under argon. After cooling the resulting solution at 0° C., a solution of triphenylphosphine (500 mg) in anhydrous dichloromethane (10 mL) was added dropwise. The reaction mixture was stirred at room temperature for 20 h and then concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 30 g column, Si60 15-40 μm, eluted with dichloromethane/heptane, 40:60) to give 1,3-bis-bromomethyl-5-methoxy-benzene (170 mg):

Workup

concentrationconcentrated in vacuo to a residue
customThe residue was purified by silica gel chromatography (Merck SuperVarioFlash 30 g column, Si60 15-40 μm, eluted with dichloromethane/heptane, 40:60)

Sources & evidence

ORD record: ord-7a285951222740f1b97a1e512c58904e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163736B2

Reaction notes

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