Pyridine → 6-(1-Bromoethyl)-4,4-dimethylchroman

HRID 1382908

Reaction equation

HRID 1382908 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12](O)[CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1.N1C=CC=CC=1.P(Br)(Br)[Br:23].C(OCC)C>CCCCCC>[Br:23][CH:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][CH2:4][CH2:3][C:2]2([CH3:15])[CH3:1])[CH3:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 140102484,4-Dimethyl-6-(1-hydroxyethyl)chroman

Product 1

HCID 140102506-(1-Bromoethyl)-4,4-dimethylchromanYield 153.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 6.0 g (29.1 mmol) of 4,4-dimethyl-6-(1-hydroxyethyl)chroman and 1.15 g (14.5 mmol) of pyridine in 25 ml of hexane, was added 3.92 g (14.5 mmol) of phosphorus tribromide, at ca. 0° C. Stirring was continued at ca. 0° C. for 1 hour, and then the reaction mixture was poured into 500 ml of diethyl ether. The ether was washed with water, dried (MgSO4) and evaporated in vacuo to give 6.0 g (78% yield) of the title compound as an oil.

Workup

  1. customat ca. 0° C
  2. washThe ether was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2a1342534fe24399a8def04da785ad83
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Linked notes

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