4-Bromo-2-chlorophenol → O-(2-chloro-4-bromophenyl)hydroxylamine hydrochloride

HRID 2179335Notes

Reaction equation

HRID 2179335 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[NH2:10]OS(O)(=O)=O>>[ClH:9].[Cl:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[O:8][NH2:10]

Participants

3

Reactant 2

HCID 198594-Bromo-2-chlorophenolHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 68109187O-(2-chloro-4-bromophenyl)hydroxylamine hydrochlorideYield 39.8%

Procedure

4-bromo-2-chlorophenol (110 g, 0.53 mol) was reacted with hydroxylamine-O-sulfonic acid (15 g, 0.13 mol) using the procedure of Example 29, step A to give O-(2-chloro-4-bromophenyl)hydroxylamine hydrochloride (13.4 g, 28%) as a light brown solid: 1H NMR (DMSO, 400 MHz) δ 7.61 (d, J=2.0 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.47 (s, 1H), 5.81 (br s, 3H).

Sources & evidence

ORD record
ord-7de2cf3a44434301a2e2b76f2fd10413
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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