Tetrahydrofuran → 4-Bromo-α-ethenylbenzenemethanol

HRID 1534674Notes

Reaction equation

HRID 1534674 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Br:5][C:6]1[CH:13]=[CH:12]C=C[C:7]=1C=O.[CH2:14]1C[O:17][CH2:16][CH2:15]1>>[OH:17][CH:16]([C:2]1[CH:1]=[CH:7][C:6]([Br:5])=[CH:13][CH:12]=1)[CH:15]=[CH2:14]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 811292-BromobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 199101224-Bromo-α-ethenylbenzenemethanol

Conditions

Temperature
0 °C

Procedure

81 ml of a 1.6 molar solution of vinylmagnesium bromide in THF are dripped at -10° C. into a solution of 20.0 g of 4 bromobenzaldehyde in 300 ml of absolute THF. After addition the mixture is stirred for 60 minutes at 0° C., poured into ice water and extracted with ethyl acetate. After chromatography on Al2O3 with hexane/ethyl acetate 18.6 g of 4-(1-hydroxy-2-propenyl)-bromobenzene are obtained in the form of colorless oil.

Workup

  1. additionAfter addition the mixture
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-fc5ede18b9d647d0b3ef8290716bf407
Source dataset
uspto-grants-1992_02
Patent number
US05089635

Reaction notes

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