3-Bromo-5-iodobenzoic acid → (3-Bromo-5-iodophenyl)methanol

HRID 337644Notes

Reaction equation

HRID 337644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([I:11])[CH:10]=1

Participants

3

Reactant 1

HCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 15467379(3-Bromo-5-iodophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-5-iodobenzoic acid (1.0 eq.) in THF (0.2 M) at RT was added borane-methyl sulfide complex (1.5 eq). After 3 days of stirring at RT, the reaction mixture was quenched cautiously with 2 N aq. HCl and extracted with ether. The combined organic extracts were washed with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. customthe reaction mixture was quenched cautiously with 2 N aq. HCl
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with 1 N aq. NaOH, water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d1100e98bace429eb32b1bad879614dd
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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