O-Phenylenediamine → 4-Bromobenzene-1,2-diamine

HRID 620027Notes

Reaction equation

HRID 620027 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(OC(=O)C)(=O)C.[Br:16]Br.S([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:16][C:5]1[CH:4]=[CH:3][C:2]([NH2:7])=[C:1]([NH2:8])[CH:6]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 7918Acetic AnhydrideHCID 24408BromineHCID 23665763Sodium Bisulfite

Product 1

HCID 3235934-Bromobenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of o-phenylenediamine (5 g, 46.2 mmol), acetic acid (40 ml) and acetic anhydride (10.4 g, 102 mmol) was cooled in ice water, to which a solution of bromine (8.9 g, 55.4 mmol) in acetic acid (10 ml) was added and the reaction mixture was stirred for 40 minutes at 50°-55° C. and then the mixture was poured into a solution of sodium hydrogensulfite (1.5 g) in ice water (300 ml).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-db0631a066a7483691ca6a8a3fc27bc6
Source dataset
uspto-grants-1989_04
Patent number
US04818761

Reaction notes

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