Bromine → HCID 68727096, compound

HRID 1892064Notes

Reaction equation

HRID 1892064 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[C:5]([CH3:14])[CH:4]=1.[Br:15]Br>CO>[Br:15][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:14])[C:10]1=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 12696043HCID 12696043, compound

Product 1

HCID 68727096HCID 68727096, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the cold (−10° C.) solution of 7-methoxy-5-methyl-3,4-dihydro-2H-naphthalen-1-one (8.3 g, 0.04 mol) in methanol (20 mL), the solution of bromine (2.3 mL, 0.04 mol) in methanol (10 mL) was added dropwise and the mixture was stirred for 2 h while allowing the temperature to rise to room temperature. Methanol was evaporated in vacuo and the mixture was diluted with ethyl acetate and washed with aqueous sodium thiosulphate solution followed by saturated sodium bicarbonate, brine and dried. Evaporation of the solvent gave 2-bromo-7-methoxy-5-methyl-3,4-dihydro-2H-naphthalen-1-one as an off-white solid, 10 g, which was used as such in step 2. MS m/z 271 (M+2).

Workup

  1. customto rise to room temperature
  2. customMethanol was evaporated in vacuo
  3. additionthe mixture was diluted with ethyl acetate
  4. washwashed with aqueous sodium thiosulphate solution
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-56a86e96097d47cab1004d407a7f143e
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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