4-Bromophenol → 4-bromophenyl pivalate

HRID 2188233Notes

Reaction equation

HRID 2188233 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C1COCC1>[C:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 3182174-bromophenyl pivalateYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.02 g of 4-bromophenol (0.116 mol) in 100 mL of dry THF was treated with 15.0 mL of pivaloyl chloride (0.126 mol), followed by 35.5 mL of triethylamine (0.255 mol). A large amount of white solid precipitated so 50 mL of additional THF was added to the mixture to afford a free-flowing slurry. The reaction mixture was filtered and the precipitate was washed with 200 mL THF and then discarded. The filtrate was concentrated in vacuo to a liquid which solidified when dried under reduced pressure to yield 30.5 g (100%) of 4-bromophenyl pivalate.

Workup

  1. customA large amount of white solid precipitated so 50 mL of additional THF
  2. additionwas added to the mixture
  3. customto afford a free-flowing slurry
  4. filtrationThe reaction mixture was filtered
  5. washthe precipitate was washed with 200 mL THF
  6. concentrationThe filtrate was concentrated in vacuo to a liquid which
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-94472d2ddfe54bc78e2775b044c46ac0
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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