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

HRID 1669427Notes

Reaction equation

HRID 1669427 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].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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

2-Bromo-5-methoxy benzoic acid (1 eq) was dissolved in anhydrous THF (0.55M solution) and BH3SMe2 complex (2M in THF, 1 eq) was added dropwise to the solution. The mixture was stirred 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 colourless oil was obtained (94%), which was used without further characterization in the next reaction.

Workup

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

Sources & evidence

ORD record
ord-2020ec3107434368b983e60414eec8fd
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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