Water → (5-Bromo-2-iodophenyl)methanol

HRID 1270780Notes

Reaction equation

HRID 1270780 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.C1COCC1.O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3029395-Bromo-2-iodobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 15339730(5-Bromo-2-iodophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-iodobenzoic acid (100 g, 0.306 mol) is dissolved in THF (350 mL) and cooled in an ice bath. Borane-THF complex (460 mL of 1 M in THF, 0.460 mol) is added dropwise. After addition is complete, the reaction is warmed to room temp and stirred for 14 hours. The mixture is transferred a large erlenmeyer flask (4 L), cooled in an ice bath and carefully quenched with water (250 mL). Evaporation of the THF by rotary evaporator gives a white suspension which is treated with additional water (1 L) and then filtered and dried in a vacuum dessicator over P2O5 to give 5-bromo-2-iodobenzyl alcohol.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. temperaturecooled in an ice bath
  4. customcarefully quenched with water (250 mL)
  5. customEvaporation of the THF
  6. customby rotary evaporator
  7. customgives a white suspension which
  8. filtrationfiltered
  9. dry with materialdried in a vacuum dessicator over P2O5

Sources & evidence

ORD record
ord-eaf6c08ade7e47c8928637ee389c074c
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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