1-Bromo-3-methylbutane → HCID 78878307, compound

HRID 1454099Notes

Reaction equation

HRID 1454099 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19]>CN(C)C=O>[CH2:16]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:12])=[CH:6][CH:7]=1)[CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 78878307HCID 78878307, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl-4-hydroxyphenylacetate (2.00 g, 12.0 mmol) was added in one portion to a stirred suspension of sodium hydride (60% mineral oil suspension; 528 mg, 13.2 mmol) in dimethylformamide (20 mL) at room temperature under nitrogen. After stirring for 30 min 1-bromo-3-methylbutane (1.99 g, 1.58 mL, 13.2 mmol) was added dropwise over 5 min then stirring was continued for 12 h. The volatiles were evaporated then the residue partitioned between dichloromethane (50 mL) and water (50 mL). The phases were separated and the aqueous phase was washed with dichloromethane (2×50 mL). The organics were combined, dried (magnesium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (20% diethyl ether: cyclohexane) to give the title compound as a colourless oil (2.16 g, 76%). LC/MS: 3.51 min; z/e 254, calcd (M+18) 254. 1H NMR (400 MHz: CDCl3): 7.15 (2H), 6.85 (2H), 4.00 (2H), 3.70 (3H), 3.55 (2H), 1.85 (1H), 1.70 (2H), 0.95 (6H).

Workup

  1. additionwas added dropwise over 5 min
  2. customThe volatiles were evaporated
  3. customthe residue partitioned between dichloromethane (50 mL) and water (50 mL)
  4. customThe phases were separated
  5. washthe aqueous phase was washed with dichloromethane (2×50 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent evaporated
  8. customThe residue was chromatographed on silica gel (20% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-6e5713e4499045bd94c9cae86fd0bd8c
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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