3-Bromophenol → Methyl 2-(3-bromophenoxy)-4-methylpentanoate

HRID 1744061Notes

Reaction equation

HRID 1744061 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].Br[CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C1COCC1.C(OCC)C.O.C(=O)(O)[O-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([O:19][CH3:20])=[O:18]

Participants

9

Reactant 3

HCID 115633-BromophenolHCID 12957039Methyl 2-bromo-4-methylpentanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22235997Methyl 2-(3-bromophenoxy)-4-methylpentanoate

Reagents, catalysts & solvents 5

HCID 769Bicarbonate IonSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromophenol (2.99 g, 17 mmoles) in a mixture of DMF (3 mL) and THF (15 mL) was treated with potassium tert-butoxide (1.85 g, 16.5 mmoles) and stirred for 30 minutes. Methyl 2-bromo-4-methylpentanoate (2.5 mL, 15.75 mmoles) was added in one portion and the reaction was stirred overnight. The reaction was diluted with diethyl ether, water and sat. aq. bicarbonate. The phases were separated and the organic phase was washed with 2 portions of 1.2 N hydrochloric acid and then brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue which was purified by flash chromatography to give methyl 2-(3-bromophenoxy)-4-methylpentanoate.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe phases were separated
  3. washthe organic phase was washed with 2 portions of 1.2 N hydrochloric acid
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-501cb777237344d1be28d3a2c737cee8
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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