Hydrogen Bromide → HCID 18385099, compound

HRID 2298238Notes

Reaction equation

HRID 2298238 reaction equation
C(O[CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([N:22]2[C:26]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=4)[N:29]([CH3:37])[CH:28]=3)=[N:25][NH:24][C:23]2=[O:38])=[CH:13]1)C1C=CC=CC=1.[BrH:39]>C(O)(=O)C>[Br:39][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([N:22]2[C:26]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=4)[N:29]([CH3:37])[CH:28]=3)=[N:25][NH:24][C:23]2=[O:38])=[CH:13]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 18385121HCID 18385121, compound

Product 1

HCID 18385099HCID 18385099, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

In a flask was added the compound obtained in Example 1, (1.0 g, 2.36 mmol) in acetic acid (30 mL). To this solution was added hydrobromic acid (33% in acetic acid, 8 mL), and the flask was sealed. The flask was heated with stirring in an oil bath (80° C.) for 12 hours. The reaction was monitored on LC-MS, which confirmed the completion of the reaction. The volatiles were removed in vaccuo, and the residue was partitioned between ethyl acetate and water (50+50 mL). The organic phase was washed twice with water and once with brine and evaporated to give a 1.1 g (97%) of the title compound as a crude product, pure enough to be used further without purification.

Workup

  1. customthe flask was sealed
  2. temperatureThe flask was heated
  3. customthe completion of the reaction
  4. customThe volatiles were removed in vaccuo
  5. customthe residue was partitioned between ethyl acetate and water (50+50 mL)
  6. washThe organic phase was washed twice with water and once with brine
  7. customevaporated

Sources & evidence

ORD record
ord-3eb797f0639c4614999a0a9273a35c7c
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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