Dichloromethane → 3,4-Difluoro-2-(2-hydroxyethyl)nitrobenzene

HRID 2184186Notes

Reaction equation

HRID 2184186 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH2:14][C:15](O)=[O:16].C(Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH2:14][CH2:15][OH:16]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium Bicarbonate2×HCID 4311764Sodium borohydrideHCID 22475350(2,3-Difluoro-6-nitrophenyl)acetic acid

Product 1

HCID 224753203,4-Difluoro-2-(2-hydroxyethyl)nitrobenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of NaBH4 (3.60 g, 95.4 mmol) in THF (12 mL) cooled below 10° C. was added a solution of 2-(2,3-difluoro-6-nitrophenyl)acetic acid (10.9 g, 50.2 mmol), as prepared in the preceding step, in THF (4 mL) over a period of 1 hour. To this mixture was added a solution of boron trifluoride diethyl etherate complex (16.5 mL, 131 mmol) in THF (24 mL) over a period of 1 hour, keeping the reaction temperature below 10° C. After the addition the reaction was continued to stir on ice for 15 minutes, and then at ambient temperature for 20 minutes. To a mixture of DCM (180 mL) and H2O (140 mL) was added NaHCO3 (15 g, 179 mmol). The reaction mixture was slowly added to the above NaHCO3 solution and stirred overnight. The organic layer was separated, dried over Na2SO4, and concentrated to give the title compound (10.1 g, 99% yield) as light brown oil. 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, J=9.1, 4.4 Hz, 1H), 7.27-7.18 (m, 1H), 3.95 (t, J=6.3 Hz, 2H), 3.30-3.27 (m, 2H), 1.82 (s, 1H).

Workup

  1. temperaturecooled below 10° C.
  2. customthe reaction temperature below 10° C
  3. additionAfter the addition the reaction
  4. waitat ambient temperature for 20 minutes
  5. stirringstirred overnight
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c14e7dedf630496d97e71f7d7753e3f1
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

Loading…