Isobutane → Tert-butyl 4-bromo-3-methylbenzoate

HRID 2282337Notes

Reaction equation

HRID 2282337 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[CH3:11].[K].[O-:13]CCCC.[CH:18]([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:13][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 6360IsobutaneHCID 5462222PotassiumHCID 70215344-Bromo-3-methylbenzoyl chlorideHCID 12476378Butan-1-olate

Product 1

HCID 11845988Tert-butyl 4-bromo-3-methylbenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the above 4-bromo-3-methylbenzoyl chloride residue in THF (100 mL), a solution of potassium ten-butoxide (6.0 g, 53.5 mmol) in THF (60 mL) was added dropwise at 0° C. under nitrogen. The mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over Na2SO4. The compound was purified by silica column chromatography using heptane and ethyl acetate as eluent to give a yield of 96%. 1HNMR (300 MHz, CD2Cl2): δ 7.88 (s, 1H), 7.53-7.7 (m, 2H), 2.42 (s, 3H, CH3), 1.57 (s, 9H, CH3); MS (m/e): calculated 215.96/213.96 (1:1). found 215.0/217.0 (1:1), for [M+H−tBu]+.

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe compound was purified by silica column chromatography
  6. customto give a yield of 96%

Sources & evidence

ORD record
ord-9badc87120744d3896d9f06db761a0d3
Source dataset
uspto-grants-2015_09
Patent number
US09139868B2

Reaction notes

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