Hydrochloric Acid → (5-Chloro-2-iodophenyl)methanol

HRID 1388544Notes

Reaction equation

HRID 1388544 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[BH4-].[Na+].B(F)(F)F.CCOCC.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[CH2:7][OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 1394515-Chloro-2-iodobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 818020(5-Chloro-2-iodophenyl)methanolYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 120 g of 5-chloro-2- iodobenzoic acid (K. Pelz et al., Collect.Czech.Chem.Commun. 33, 1852, 1968) in 145 ml of tetrahydrofuran is stirred and treated at 10°-20° C. for 45 minutes with 16.1 g of sodium borohydride. The mixture is then stirred for 30 minutes at this temperature and treated with a solution of 80.3 g (71.4 ml) of boron trifluoride etherate in 40 ml of tetrahydrofuran. It is stirred for another 3 hours and while cooling with ice-cold water it is decomposed at a maximum temperature of 8° C. with 50 ml of 5% hydrochloric acid added dropwise. It is diluted with water and extracted with benzene. The extract is washed with a 5% sodium hydroxide solution and water, dried with magnesium sulfate and evaporated. There are obtained 100 g (96%) of crude 5-chloro-2-iodobenzyl alcohol with m.p. of 115°-117° C. The analytically pure substance is obtained by crystallization from ethanol; m.p. 116°-117° C.

Workup

  1. stirringIt is stirred for another 3 hours
  2. temperaturewhile cooling with ice-cold water it
  3. additionadded dropwise
  4. extractionextracted with benzene
  5. washThe extract is washed with a 5% sodium hydroxide solution and water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-99f28071720d4d7784841912c08f7850
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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