Ammonium Chloride → 5-Bromobenzene-1,3-diamine

Temperature

80 °C

Ammonium chloride (5.20 g, 97 mmol) was added to a stirred, cooled (room temperature) mixture of 1-bromo-3,5-dinitrobenzene (20 g, 81 mmol) and iron (54.3 g, 972 mmol) in ethanol:water (2:1) and the mixture was stirred at 80° C. for 1 h. The heterogeneous reaction was filtered on celite while hot, concentrated, and diluted with brine. The product was extracted with ethyl acetate, the organic layer washed with brine and dried over Na2SO4. The residue was dissolved in boiling ethyl acetate (˜75 mL), a bit of hexanes was added to form a layer on top of ethyl acetate (˜7.5 mL) and the mixture was left to crystallize overnight. The crystals were filtered, washed with diethyl ether and air-dried to give 5.77 g of 5-bromobenzene-1,3-diamine as a grey solid. MS ESI: [M+H]+ m/z 187.0 and 189.0.

1. temperaturecooled
2. customThe heterogeneous reaction
3. filtrationwas filtered on celite while hot,
4. concentrationconcentrated
5. additiondiluted with brine
6. extractionThe product was extracted with ethyl acetate
7. washthe organic layer washed with brine
8. dry with materialdried over Na2SO4
9. dissolutionThe residue was dissolved
10. additiona bit of hexanes was added
11. customto form a layer on top of ethyl acetate (˜7.5 mL)
12. waitthe mixture was left
13. customto crystallize overnight
14. filtrationThe crystals were filtered
15. washwashed with diethyl ether
16. customair-dried

ORD record

ord-32b0345036224e5dbac96c58c303e463

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2