Hydrogen Bromide → 1-Bromo-3-fluorobenzene

HRID 466816

Reaction equation

HRID 466816 reaction equation
BrBr.[F:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1N.FC1C=CC(N)=CC=1.FC1C=C(F)C=CC=1N.[Br:28]C1C=C(F)C=CC=1N.[BrH:37].BrC1C=CC(N)=C([F:46])C=1.BrC1C=C(F)C=C(F)C=1N.N([O-])=O.[Na+].O[PH2]=O>>[Br:28][C:7]1[CH:5]=[C:4]([F:3])[CH:10]=[CH:9][CH:8]=1.[Br:37][C:9]1[CH:10]=[C:4]([F:3])[CH:5]=[C:7]([F:46])[CH:8]=1

Participants

12

Reactant 10

HCID 260Hydrogen Bromide3×HCID 95842-FluoroanilineHCID 97092,4-DifluoroanilineHCID 97314-FluoroanilineHCID 24408Bromine2×HCID 1230504-Bromo-2-fluoroanilineHCID 1362852-Bromo-4,6-DifluoroanilineHCID 2428732-Bromo-4-fluoroanilineHCID 4124402Phosphinic AcidHCID 23668193Sodium Nitrite

Product 2

HCID 140821-Bromo-3-fluorobenzeneHCID 1363131-Bromo-3,5-difluorobenzene

Procedure

In a particularly preferred embodiment of the present invention, Br2 is mixed with a starting material selected from the group consisting of 2-fluoroaniline, 4-fluoroaniline, 2,4-difluoroaniline or a mixture thereof. The Br2 is reacted with the selected starting material to form a corresponding intermediate material selected from the group consisting of 2-bromo-4-fluoroaniline.HBr, 4-bromo-2-fluoroaniline.HBr, 2-bromo-4,6-difluoroaniline.HBr and mixtures thereof. The resulting intermediate material then is mixed with a deaminating agent comprising NaNO2 and H3PO2. The intermediate material then is deaminated, under deaminating conditions, so as to form the desired end product, 3-bromofluorobenzene or 1-bromo-3,5-difluorobenzene.

Workup

  1. customto form a corresponding intermediate material
  2. additionThe resulting intermediate material then is mixed with a deaminating agent

Sources & evidence

ORD record
ord-330c0560309d4a5d90b1cd6b20bc63a9
Source dataset
uspto-grants-1992_10
Patent number
US05157169

Linked notes

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