6-BROMO-2,3-DIHYDRO-BENZOFURAN

6-BROMO-2,3-DIHYDRO-BENZOFURAN Property

Boiling point:

239.8±29.0 °C(Predicted)

Density 

1.582±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

InChI

InChI=1S/C8H7BrO/c9-7-2-1-6-3-4-10-8(6)5-7/h1-2,5H,3-4H2

InChIKey

BQWBDYZMUCSEHK-UHFFFAOYSA-N

SMILES

O1C2=CC(Br)=CC=C2CC1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

6-BROMO-2,3-DIHYDRO-BENZOFURAN Chemical Properties,Usage,Production

Uses

6-Bromo-2,3-dihydrobenzofuran is used in the preparation of 2-alkylamino nicotinamide analogs as orally active ghrelin receptor (ghrelinR) inverse agonists.

Synthesis

GENERAL STEPS: A hexane solution of 1.6 M n-butyllithium (21.84 mL, 34.94 mmol) was slowly added dropwise to a solution of tetrahydrofuran (THF, 200 mL) of 1,4-dibromo-2-(2-bromoethoxy)benzene (10.45 g, 29.12 mmol) under argon protection, maintaining the reaction temperature at -78 °C. The reaction was carried out by stirring the reaction mixture for 30 minutes. After dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 30 min, followed by warming up to 0 °C and stirring for 2 hours. After completion of the reaction, the mixture was poured into ice water and the pH was adjusted to 3 with 2 N hydrochloric acid. next, the aqueous phase was extracted three times with a solvent mixture of ethyl acetate/hexane (3:1, v/v). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography using gradient elution (2%→8% ethyl acetate/hexane) to afford 6-bromo-2,3-dihydrobenzofuran (4.57 g, 22.96 mmol, 79% yield) as a white solid.

References

[1] Patent: WO2009/7399, 2009, A1. Location in patent: Page/Page column 86
[2] Patent: EP2862571, 2015, A1. Location in patent: Paragraph 0146; 0147
[3] Patent: US2015/166559, 2015, A1. Location in patent: Paragraph 0200; 0201
[4] Patent: TW2016/2105, 2016, A. Location in patent: Paragraph 1108
[5] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 34