7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 2089470Notes

Reaction equation

HRID 2089470 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])=[CH:4][CH:3]=1.[BH4-].[Na+]>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])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 126949197-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-3,4-dihydro-2H-naphthalen-1-one (CAS#32281-97-3, 3.5 g, 0.015 mol) in methanol (7 mL) and dichloromethane (10 mL) at 0° C. is added sodium borohydride (1.47 g, 0.038 mol) in one portion. The cooling bath is removed and after 1.5 hours, the mixture is poured into water and the volatile organics are removed in vacuo. Extraction with dichloromethane, drying over sodium sulfate, filtering through a cotton plug and concentration in vacuo affords 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol. 1H NMR (400 MHz, CDCl3) δ ppm 1.72 (d, J=6.3 Hz, 1 H), 1.74-1.90 (m, 2 H), 1.92-2.07 (m, 2 H), 2.62-2.71 (m, 1 H), 2.73-2.82 (m, 1 H), 4.73-4.77 (m, 1 H), 6.98 (d, J=8.2 Hz, 1 H), 7.31 (dd, J=8.2, 2.1 Hz, 1 H), 7.61 (d, J=2.1 Hz, 1 H).

Workup

  1. customThe cooling bath is removed and after 1.5 hours
  2. additionthe mixture is poured into water
  3. customthe volatile organics are removed in vacuo
  4. extractionExtraction with dichloromethane
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering through a cotton plug and concentration in vacuo

Sources & evidence

ORD record
ord-ca61a6ed43864922897a1d1ee269a7ad
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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