Methanol → (2-Fluoro-6-iodophenyl)methanol

HRID 1363154Notes

Reaction equation

HRID 1363154 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([I:11])[C:3]=1[C:4](O)=[O:5].CSC.B.CO>C1COCC1.COB(OC)OC>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([I:11])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 27333022-Fluoro-6-iodobenzoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 59705003(2-Fluoro-6-iodophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8470Trimethyl borateSolvent

Conditions

Temperature
22.5 °C

Procedure

To a stirred solution of 2-fluoro-6-iodobenzoic acid (10 mmol) in THF (6.5 mL) and trimethylborate (3.25 mL) was added borane dimethylsulfide (12 mmol) slowly, maintaining the internal temperature at 20-25° C. Stirring was continued for an additional 16 h at room temperature and then methanol (1.44 mL) was added cautiously. The resulted solution was evaporated in vacuo to offer 2.5 g of the title compound as a pale yellow oil.

Workup

  1. customThe resulted solution was evaporated in vacuo

Sources & evidence

ORD record
ord-52199c7415654bbab26adb125b52999e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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