Hydrochloric Acid → (2-Bromo-5-methoxyphenyl)methanol

HRID 1518246Notes

Reaction equation

HRID 1518246 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].CSC.B.Cl>C1COCC1.CO>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 899062-Bromo-5-methoxybenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-5-methoxy benzoic acid (1 eq.) was dissolved in anhydrous THF (0.55M solution) and borane dimethylsulfide complex (2M in THF, 1 eq.) was added dropwise to the solution. The mixture was left stirring overnight, then HCl in MeOH was added and the mixture was warmed to 60° C. All volatiles were evaporated and the residual material was dissolved in DCM. The solution was washed with 1N HCl and with brine, then dried over Na2SO4 and evaporated in vacuo. A colorless oil was obtained (94%), which was used without further characterization in the next reaction.

Workup

  1. waitThe mixture was left
  2. customAll volatiles were evaporated
  3. dissolutionthe residual material was dissolved in DCM
  4. washThe solution was washed with 1N HCl and with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customA colorless oil was obtained (94%), which
  8. customwas used without further characterization in the next reaction

Sources & evidence

ORD record
ord-db39e85129e14fc3b0d0f95a92c54297
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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