3-BROMO-PHENYL ACETATE Chemical Properties

Boiling point:

149℃ (40 Torr)

Density 

1.501±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

108.0±22.6℃

storage temp. 

Store at room temperature

Appearance

Light yellow to yellow Liquid

3-BROMO-PHENYL ACETATE Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1542, 1983 DOI: 10.1021/jo00157a035

Synthesis

1. Acetyl chloride (61.7 mL, 867 mmol) was added dropwise to a solution of 3-bromophenol (150 g, 867 mmol) and pyridine (70.0 mL, 867 mmol) in dichloromethane (1000 mL) in an ice bath over a controlled time period of 1 hour. After the dropwise addition, the reaction mixture was stirred at room temperature for 18 hours. 2. After completion of the reaction, water (500 mL) was added to the reaction mixture for dilution and the organic layer was separated. The aqueous layer was extracted with dichloromethane (4 x 150 mL) and the organic layers were combined. 3. The combined organic layers were washed sequentially with 2.5N NaHSO4 (3×150mL), 3N NaOH (3×150mL), water (2×200mL) and brine (2×200mL). 4. The washed organic layer was dried over anhydrous Na2SO4, filtered and the solvent was evaporated to give phenyl 3-bromoacetate as a pink liquid (36.0 g, 86% yield). 5. The product was characterized by GC/MS and 1H NMR: GC/MS data: m/z 214 (M)+ (C8H7BrO2 calculated value 215.04). 1H NMR (DMSO-d6) δ: 7.44-7.48 (ddd, 1H, J1=1.0Hz, J2=2.0Hz, J3=8.1Hz, Ar-H), 7.43 (t, 1H, J1=1.0Hz, J2=2.0Hz, Ar-H). (t, 1H, J=2.1Hz, Ar-H), 7.38 (t, 1H, J=8.1Hz, Ar-H), 7.14-7.18 (ddd, 1H, J1=1.0Hz, J2=2.2Hz, J3=8.1Hz, Ar-H), 2.26 (s, 3H, CH3).

References

[1] Patent: WO2007/88450, 2007, A2. Location in patent: Page/Page column 21
[2] Patent: US2009/202478, 2009, A1
[3] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 293
[4] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 5, p. 323 - 329
[5] Patent: US2008/188521, 2008, A1. Location in patent: Page/Page column 12

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