Trimethylsilyl iodide → 4-(Bromomethyl)cyclohexan-1-ol

HRID 1289349Notes

Reaction equation

HRID 1289349 reaction equation
C[O:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][Br:10])[CH2:5][CH2:4]1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[Br:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([OH:2])[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 217065291-(Bromomethyl)-4-methoxycyclohexane

Product 1

HCID 218327074-(Bromomethyl)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 4-methoxycyclohexylbromomethane compound (C-4) (2.6 g) in chloroform (7.8 g) was cooled with ice. Then trimethylsilyliodide (2.2 ml) was transferred to the C-4 solution. It was stirred at ambient temperature for 8 h, and then quenched with methanol. Then, volatiles were removed to obtain the desired alcohol in almost quantitative yield.

Workup

  1. customquenched with methanol
  2. customThen, volatiles were removed

Sources & evidence

ORD record
ord-7df562be99754e0aaf4e0a7c5c27f733
Source dataset
uspto-grants-1998_05
Patent number
US05750300

Reaction notes

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