Hydrogen Bromide → (Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-hydroxy-acrylic acid

HRID 1515066Notes

Reaction equation

HRID 1515066 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](/[CH:12]=[C:13](\[O:17]C)/[C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[Cl:19].Br>C(O)(=O)C.O>[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](/[CH:12]=[C:13](\[OH:17])/[C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[Cl:19]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 67043265(Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-methoxy-acrylic acid

Product 1

HCID 58202069(Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-hydroxy-acrylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

10.00 kg (33.82 mol) (Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-methoxy-acrylic acid (C) were suspended in 20.0 L acetic acid and heated to 80° C., before 57.02 kg (338.25 mol) hydrobromic acid (48%) were added. Then the reaction mixture was stirred for 1.5 hours at 80° C., then diluted with 78.0 L water and the suspension was cooled to 22° C. The product was separated off, washed with 100.0 L water and dried.

Workup

  1. additionwere added
  2. temperaturethe suspension was cooled to 22° C
  3. customThe product was separated off
  4. washwashed with 100.0 L water
  5. customdried

Sources & evidence

ORD record
ord-ea36bc46479f4283abee476227c8716c
Source dataset
uspto-grants-2012_07
Patent number
US08222402B2

Reaction notes

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