Dichloromethane → [2-(Bromomethyl)-3-chlorophenyl]methanol

HRID 446027Notes

Reaction equation

HRID 446027 reaction equation
ClCCl.[Br:4][CH2:5][C:6]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8](OC)=[O:9].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>COC(C)(C)C>[Br:4][CH2:5][C:6]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9357Potassium Sodium TartrateHCID 110327262-Bromomethyl-3-chloro-benzoic acid methyl esterHCID 21273587HCID 21273587, compound

Product 1

HCID 22121430[2-(Bromomethyl)-3-chlorophenyl]methanolYield 98.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Dichloromethane (10 ml) was added to methyl 2-(bromomethyl)-3-chlorobenzoate obtained in Example 10c (500 mg, 1.9 mmol), a 1.04 M diisobutylaluminum hydride/n-hexane solution (4.57 ml, 4.75 mmol) was added at −78° C., followed by stirring for one hour under a nitrogen atmosphere. A saturated aqueous Rochelle salt solution and tert-butyl methyl ether were added, followed by extraction with tert-butyl methyl ether. The organic layer was washed with brine, dried over magnesium sulfate and then allowed to pass through a silica gel pad. The eluate was concentrated to give the title compound (440 mg, yield 98.3%).

Workup

  1. extractionfollowed by extraction with tert-butyl methyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-6b542f8eda9840f3ba557ec9c44a76e4
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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