Sodium Carbonate → Tert-butyl 4-(bromomethyl)benzoate

HRID 1905410Notes

Reaction equation

HRID 1905410 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:21]Br>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 116297491,1-Dimethylethyl 4-methylbenzoate

Product 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateYield 995.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

13.2 Grams (0.006 mole) of tert-butyl 4-methylbenzoate, 0.3 g (0.0012 mole) of benzoyl peroxide and 6 g (0.006 mole) of sodium carbonate were suspended in 100 ml of carbon tetrachloride, and 9.6 g (0.06 mole) of bromine was added dropwise at 50° C. over 30 minutes with stirring. After completion of the addition, reaction was continued for further 30 minutes. The reaction solution was then cooled and filtered to remove carbon tetrachloride-insoluble matters. Carbon tetrachloride was then removed by evaporation under reduced pressure to obtain 16.2 g of tert-butyl 4-bromomethylbenzoate as crystals.

Workup

  1. additionAfter completion of the addition, reaction
  2. temperatureThe reaction solution was then cooled
  3. filtrationfiltered
  4. customto remove carbon tetrachloride-insoluble matters
  5. customCarbon tetrachloride was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-c98a15938a534604983613ca18a31b53
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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