Methanol → (5-Chloro-2-iodophenyl)methanol

HRID 1058256Notes

Reaction equation

HRID 1058256 reaction equation
CSC.B.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([I:15])=[C:10]([CH:14]=1)[C:11](O)=[O:12].CO>C1COCC1.COB(OC)OC>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([I:15])=[C:10]([CH:14]=1)[CH2:11][OH:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 1394515-Chloro-2-iodobenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 818020(5-Chloro-2-iodophenyl)methanolYield 74.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8470Trimethyl borateSolvent

Conditions

Temperature
22.5 °C

Procedure

Borane methylsulfide (7.3 mL, 73 mmol) was added to a stirred solution of 5-chloro-2-iodobenzoic acid (17.17 g, 60.79 mmol) in THF (40 mL) and trimethylborate (20 mL), maintaining the internal temperature at 20-25° C. After 16 h methanol (8.87 mL, 0.219 mol) was added cautiously and the solution was evaporated in vacuo, azeotroping with methanol (3×50 mL). The resulting solid was recrystallized (hexanes/ethyl acetate, 5:1, 120 mL) to give 5-chloro-2-iodobenzyl alcohol (12.2 g): 1H NMR (CDCl3, 400 MHz) δ 2.00 (br s, 1H), 4.64 (s, 2H), 7.00 (dd, J=2.6, 8.4 Hz, 1H), 7.49 (d, J=2.4, 1H), 7.72 (d, J=8.2 Hz, 1H).

Workup

  1. customthe solution was evaporated in vacuo
  2. customazeotroping with methanol (3×50 mL)
  3. customThe resulting solid was recrystallized (hexanes/ethyl acetate, 5:1, 120 mL)

Sources & evidence

ORD record
ord-66d12ce47df14dc0814bc69945b67022
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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