Dichloromethane → (2-Chloro-3-nitrophenyl)methanol

HRID 659653Notes

Reaction equation

HRID 659653 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7].B(F)(F)F.CCOCC.C(Cl)Cl>C1COCC1.CO>[Cl:3][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][OH:7]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 198702-Chloro-3-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 15132843(2-Chloro-3-nitrophenyl)methanolYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A 500-mL 3-necked round-bottom flask was charged with a solution of NaBH4 (4 g, 105.26 mmol, 2.10 equiv) in THF (100 mL). To this was added a solution of 2-chloro-3-nitrobenzoic acid (10 g, 49.75 mmol) in THF (100 mL) at 0° C. After 10 minutes, BF3.Et2O (15 mL) in THF (50 mL) was added dropwise over 10 minutes. The resulting solution was stirred at room temperature overnight. The reaction progress was monitored by TLC (DCM: MeOH=5:1). Upon completion, the reaction was quenched with water (500 mL) and extracted with ethyl acetate (3×300 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator affording (2-chloro-3-nitrophenyl)methanol as light yellow solid (9 g, 98%).

Workup

  1. customUpon completion, the reaction was quenched with water (500 mL)
  2. extractionextracted with ethyl acetate (3×300 mL)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-27cfc83745fd4913ba2eb5e4eaa828e8
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

Loading…