METHYL 3-BROMO-5-(HYDROXYMETHYL)BENZOATE Chemical Properties

Boiling point:

354.2±32.0 °C(Predicted)

Density 

1.557±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.08±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H9BrO3/c1-13-9(12)7-2-6(5-11)3-8(10)4-7/h2-4,11H,5H2,1H3

InChIKey

PWAJHVDGAMQOPF-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(CO)=CC(Br)=C1

Safety Information

HS Code 

2916399090

METHYL 3-BROMO-5-(HYDROXYMETHYL)BENZOATE Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 3-bromo-5-(hydroxymethyl)benzoate from methyl 3-amino-5-(hydroxymethyl)benzoate: Methyl 3-amino-5-(hydroxymethyl)benzoate (2.4 g, 13.2 mmol) was dissolved in anhydrous acetonitrile (10 mL) and slowly added dropwise to a solution of acetonitrile (20 mL) containing copper(II) bromide (3.54 g, 15.8 mmol) and tert-butyl nitrite (2.24 mL, 18.9 mmol). (2.24 mL, 18.9 mmol) in acetonitrile (20 mL), and the reaction temperature was maintained at 65 °C. The reaction mixture was stirred at 65 °C. The reaction mixture was stirred at 65 °C for 30 min, then cooled to room temperature and subsequently poured into 1N hydrochloric acid solution and extracted with ether. The organic layers were combined, washed with brine (2 times), dried over anhydrous sodium sulfate and concentrated. Purification by silica gel column chromatography (eluent: 30% ethyl acetate/hexane) afforded the target product methyl 3-bromo-5-(hydroxymethyl)benzoate 2.0 g in 62% yield. The product was identified by 1H-NMR (CDCl3, 300 MHz): δ 8.04 (s, 1H), 7.90 (s, 1H), 7.69 (s, 1H), 4.70 (s, 2H), 3.89 (s, 3H). Mass spectrometry analysis showed a molecular ion peak of 246.98 (MH)+.

References

[1] Patent: US2007/249607, 2007, A1. Location in patent: Page/Page column 85

METHYL 3-BROMO-5-(HYDROXYMETHYL)BENZOATE(307353-32-8)Related Product Information

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