Water → 7-bromo-5-fluoro-3,4-dihydro-2H-naphthalen-1-ol

HRID 2089482Notes

Reaction equation

HRID 2089482 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[C:4]([F:13])[CH:3]=1.[BH4-].[Na+].O>CO.ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[OH:12])=[C:4]([F:13])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 591994027-Bromo-5-fluoro-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 675473967-bromo-5-fluoro-3,4-dihydro-2H-naphthalen-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-5-fluoro-3,4-dihydro-2H-naphthalen-1-one (0.290 g, 1.145 mmol) in methanol (8 mL) and dichloromethane (2 mL) at 0° C. is added sodium borohydride (0.066 g, 1.718 mmol) in one portion. After 2 hours at 0° C., water (30 mL) is added and the volatile organics are removed in vacuo. The resulting mixture is extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated to afford 7-bromo-5-fluoro-3,4-dihydro-2H-naphthalen-1-ol, which is used in the next step without further purification.

Workup

  1. customthe volatile organics are removed in vacuo
  2. extractionThe resulting mixture is extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd8bc7b5dc99437a8450a26b02791df5
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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