Hydrochloric Acid → 1,2,3-Trichloro-5-(trifluoromethyl)benzene

HRID 65339

Reaction equation

HRID 65339 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:7]([Cl:17])=[C:8]([Cl:16])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.[ClH:18]>O>[Cl:18][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([Cl:16])[C:7]=1[Cl:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 130592762,3-Dichloro-5-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 27333991,2,3-Trichloro-5-(trifluoromethyl)benzeneYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of sodium nitrite (39 g.) in water (85 ml.) is added over 1 hour to a solution of 5-amino-3,4-dichloro-α,α,α-trifluorotoluene (117.5 g., 0.51 mol) in 1700 ml. concentrated hydrochloric acid at -6° C. and the solution stirred for 1 hour then filtered. The filtrate is added to a solution of cuprous chloride (76.5 g.) in concentrated hydrochloric acid (500 ml.) over 5 minutes at 0° to 8° C. and gradually heated to 80° C. over 80 minutes. The reaction mixture is cooled to 35° C. and extracted with hexane (2×300 ml.). The extract is washed with water, 2% sodium hydroxide solution, dried and distilled to give 3,4,5-trichloro-α,α,α-trifluorotoluene (70 g., 55%) b.p. 82°-86° C./10 mm, 95% pure.

Workup

  1. filtrationthen filtered
  2. additionThe filtrate is added to a solution of cuprous chloride (76.5 g.) in concentrated hydrochloric acid (500 ml.) over 5 minutes at 0° to 8° C.
  3. temperatureThe reaction mixture is cooled to 35° C.
  4. extractionextracted with hexane (2×300 ml.)
  5. washThe extract is washed with water, 2% sodium hydroxide solution
  6. customdried
  7. distillationdistilled

Sources & evidence

ORD record
ord-9f5e5083f00545fc9101c832d7d6f13b
Source dataset
uspto-grants-1986_09
Patent number
US04613360

Linked notes

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