3-Bromo-4,5-diaminobenzotrifluoride → HCID 178506064, compound

HRID 913903Notes

Reaction equation

HRID 913903 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([NH2:12])[C:3]=1[NH2:13].[N:14]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[C:3]2[NH:13][N:14]=[N:12][C:4]=2[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 7357853-Bromo-4,5-diaminobenzotrifluorideHCID 23668193Sodium Nitrite

Product 1

HCID 178506064HCID 178506064, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a cooled (15° C.) solution of 3-bromo-5-(trifluoromethyl)benzene-1,2-diamine (1.82 g, 7.14 mmol) in acetic acid (20 mL) was added a solution of sodium nitrite (0.517 g, 7.49 mmol) in water (10 mL). After 15 min, the product was collected by filtration and washed with 65% HOAc in water and air dried to give 1.5 g (79%) as a faint pink powder. 1H-NMR (4:1 CDCl3/CD3OD, 500 MHz) δ 8.08 (s, 1H), 7.71 (s, 1H), 4.23 (bs, 1H); 13C-NMR (4:1 CDCl3/CD3OD, 126 MHz) δ 139.9, 129.0 (q, J=33 Hz), 125.3, 123.3 (q, J=273 Hz), 113.4, 108.2. Mass spec.: 265.82 (MH)+.

Workup

  1. filtrationthe product was collected by filtration
  2. washwashed with 65% HOAc in water and air
  3. customdried
  4. customto give 1.5 g (79%) as a faint pink powder

Sources & evidence

ORD record
ord-253e6fef4b384e96b86336466b9790b3
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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