Allyl bromide → 13990-72-2

HRID 1772236Notes

Reaction equation

HRID 1772236 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 63734213990-72-2Yield 61.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Into a 1 L round-bottomed flask containing 500 ml of acetonitrile was added 4-fluorophenol (30.0 g, 267.6 mmol), 3-bromoprop-1-ene (41.7 g, 344.7 mmol, 1.3 eq), and potassium carbonate (55 g, 398 mmol, 1.5 eq). The mixture was stirred for 3.5 hours at 60° C. (oil bath). The solids were filtered off and the filtrate was concentrated under vacuum leaving 25.0 grams of the crude product as a yellow oil; 61%.

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c423d939987f485aba1e1e9b186ed73b
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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