Acetic Acid → Diethyl 4-[(2-bromo-6-fluorophenyl)imino]heptanedioate

HRID 1944026Notes

Reaction equation

HRID 1944026 reaction equation
C(O[C:4](OCC)([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[Br:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:24]=1[NH2:25].C(O)(=O)C>>[Br:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:24]=1[N:25]=[C:4]([CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 27829402-Bromo-6-fluoroanilineHCID 59487222Diethyl 4,4-diethoxyheptanedioate

Product 1

HCID 59487249Diethyl 4-[(2-bromo-6-fluorophenyl)imino]heptanedioate

Conditions

Temperature
145 °C

Procedure

To the ketal of Step 1 (8.46 kg, 24.31 mol), were charged 2-bromo-6-fluoroaniline (2.509 L, 22.10 mol) and acetic acid (0.253 L, 4.42 mol) under nitrogen. The mixture was heated to 145° C. and ethanol was removed by distillation. The product was used in the next reaction.

Workup

  1. customethanol was removed by distillation
  2. customThe product was used in the next reaction

Sources & evidence

ORD record
ord-880fbc829cb54b28ad550f2ac7dd300d
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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