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

HRID 570647Notes

Reaction equation

HRID 570647 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-2e08a158bd3d4d6da164223390b0346b
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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