ChemicalBook CAS DataBase List 1-(BROMOMETHYL)-3-PHENOXYBENZENE

1-(BROMOMETHYL)-3-PHENOXYBENZENE synthesis

9synthesis methods

Product Name:1-(BROMOMETHYL)-3-PHENOXYBENZENE
CAS Number:51632-16-7
Molecular formula:C13H11BrO
Molecular Weight:263.13

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51632-16-7
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Yield: 86%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane for 3 h;Reflux;

Steps:

5.2.13. 1-(Azidomethyl)-3-phenoxybenzene (13)
A solution of m-(phenoxy)toluene (3.68 g; 20 mmol) in 45 mL CCl₄ was treated with N-bromosuccinimide (5.34 g; 30 mmol) and azo-bis(isobutyronitrile) (15 mg) and the reaction mixture was refluxed for 3 h. The solution was allowed to cool to room temperature and then placed in an ice bath. A white precipitate formed which was filtered off and the filtrate was evaporated, leaving pure compound 1 as a yellow oil (4.5 g; 86% yield). ¹H NMR (CDCl₃): δ 4.4 (s, 2H), 6.9-7.41 (m, 9H). This was used in the next step. To sodium azide (3.25 g; 50 mmol) in dry DMSO (80 mL) was added compound 12 (4.5 g; 17.1 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was cooled in an ice bath and quenched with water (50 mL). The aqueous layer was extracted with ethyl ether (3 × 30 mL). The combined ethyl ether extracts were washed with water (2 × 20 mL) and dried over anhydrous sodium sulfate. The solvent was removed, leaving a crude product which was purified using flash chromatography (silica gel/methylene chloride/hexanes) to give compound 13 as a colorless oil (3.31 g; 60% yield). ¹H NMR (CDCl₃): δ 4.25 (s, 2H), 6.07-7.45 (m, 9H).

References:

Dou, Dengfeng;Mandadapu, Sivakoteswara Rao;Alliston, Kevin R.;Kim, Yunjeong;Chang, Kyeong-Ok;Groutas, William C. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 19,p. 5749 - 5755] Location in patent:experimental part

13826-35-2 Synthesis