1,2,4-Tribromobenzene → HCID 70559507, compound

HRID 931850Notes

Reaction equation

HRID 931850 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1Br.[C:10]1(=[O:14])[CH2:13][CH2:12][CH2:11]1.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:10]1([OH:14])[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 120021,2,4-TribromobenzeneHCID 14496CyclobutanoneHCID 25517Ammonium Chloride

Product 1

HCID 70559507HCID 70559507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

21.09 g (67 mmol) of 1,2,4-tribromobenzene are initially introduced in 100 ml of THF under nitrogen, cooled to −45° C., and a solution (1.3 M) of 51.54 ml (67 mmol) of isopropylmagnesium chloride/lithium chloride complex in THF is added dropwise. After 1 hour, the batch is warmed to −10° C., and 5 ml (66.34 ml) of cyclobutanone are added dropwise at this temperature. The batch is allowed to thaw, and sat. NH4Cl solution is added, the mixture is extracted with methyl t-butyl ether, the organic phase is dried over sodium sulfate and filtered, the solvent is removed in vacuo, and the residue is filtered through silica gel with dichloromethane, giving 4, which is employed in the next step without further purification.

Workup

  1. temperaturethe batch is warmed to −10° C.
  2. additionis added
  3. extractionthe mixture is extracted with methyl t-butyl ether
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. filtrationthe residue is filtered through silica gel with dichloromethane
  8. customgiving 4, which
  9. customis employed in the next step without further purification

Sources & evidence

ORD record
ord-8600dec4b476478499b3a9a01093a777
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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