Hydrogen Bromide → HCID 23203302, compound

HRID 1956753Notes

Reaction equation

HRID 1956753 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](O)=[O:9].S(Cl)([Cl:14])=O.BrN1C(=O)CCC1=O.[BrH:24]>C(Cl)(Cl)(Cl)Cl>[Br:24][CH:7]([C:8]([Cl:14])=[O:9])[CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:11]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 12328monoMethyl adipateHCID 24386Thionyl ChlorideHCID 67184N-bromobutanimide

Product 1

HCID 23203302HCID 23203302, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of adipic acid monomethyl ester (8.0 g) in carbon tetrachloride (5 ml) was added thionyl chloride (14.4 ml). The mixture was stirred at 65° C. for 30 minutes. N-Bromosuccinimide (10.7 g), carbon tetrachloride (25 ml) and 48; hydrobromic acid aqueous solution (0.5 ml) was added to the mixture. The mixture was refluxed for 1.5 hours, cooled at room temperature and filtered off. The filtrate was evaporated and distillated at reduced pressure to give methyl 5-bromo-5-chloroformylpentanoate as an oil (9.02 g).

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturecooled at room temperature
  3. filtrationfiltered off
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b382124c5583446b82010a78f26625d7
Source dataset
uspto-grants-1998_07
Patent number
US05780633

Reaction notes

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