Pyridine → HCID 13235820, compound

HRID 462881Notes

Reaction equation

HRID 462881 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:12][CH2:13][CH:14]([OH:18])[CH2:15][CH2:16][CH3:17])=[CH2:11])=[CH:6][CH:5]=1.N1C=CC=CC=1>ClCCl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH2:11][Br:1])[CH2:12][CH2:13][CH:14]([CH2:15][CH2:16][CH3:17])[O:18]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408Bromine2×HCID 132358192-(4-Chlorophenyl)-5-hydroxyoct-1-ene

Product 1

HCID 13235820HCID 13235820, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (1.28 g) in dichloromethane (25 ml) was added dropwise over 15 minutes to a stirred solution of 2-(4-chlorophenyl)-5-hydroxyoct-1-ene (1.9 g) and pyridine (0.63 g) in dichloromethane (25 ml) at 0° to 5° C. (decolourisation of bromine and mild exotherm). The cooling bath was removed and the mixture was stirred for a further 30 minutes, then washed successively with water, dilute hydrochloric acid, aqueous sodium bicarbonate, and water, then dried over magnesium sulphate and concentrated under reduced pressure to give 2-(4-chlorophenyl)-2-bromomethyl-5-prop-1-yltetrahydrofuran (2.6 g) as a red oil, 1H nmr (CDCl3): δ3.9 (2H, singlet, CH2Br).

Workup

  1. customThe cooling bath was removed
  2. washwashed successively with water, dilute hydrochloric acid, aqueous sodium bicarbonate, and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-217fb5654a3442ffaf50cfa170b4b48b
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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