Bromine → HCID 22280043, compound

HRID 1814184Notes

Reaction equation

HRID 1814184 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[S-:12][C:13]#[N:14].[Na+].[Br-].[Na+].BrBr>C(#N)C.[Cl-].[Na+].O>[S:12]([C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]([OH:11])=[CH:2][CH:3]=1)[C:13]#[N:14]

Participants

7

Reactant 4

HCID 24408BromineHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 253881Sodium BromideHCID 516871Sodium thiocyanate

Product 1

HCID 22280043HCID 22280043, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5,6,7,8-Tetrahydro-naphthalen-1-ol (1 g, 6.8 mmol) was dissolved in 25 ml acetonitrile. Sodium thiocyanate (1.76 g, 22 mmol) and sodium bromide (0.7 g, 6.8 mmol) were added and stirred for 5 minutes at ambient temperature. Bromine (1.2 g, 7.48 mmol) was added drop wise over 5 minutes. The orange solution was allowed to stir two hours. Brine was added and the crude product was extracted twice into ethyl acetate. The combined organic extracts were washed once with brine, dried over anhydrous sodium sulfate, decanted and concentrated. Normal phase chromatography afforded the title product, 1.28 g, 92%. 400 MHz 1H NMR (DMSO-d6) δ 11.1 (s, 1H), 7.40 (d, 1H, J=8.8 Hz), 6.61 (d, 1H, 8.8 Hz), 2.78 (m, 2H), 2.59 (m, 2H), 1.70 (m, 4H). MS m/z 278 (m+1). Preparation of (4-Thiocyanato-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid methyl ester (Compound TEB)

Workup

  1. stirringto stir two hours
  2. extractionthe crude product was extracted twice into ethyl acetate
  3. washThe combined organic extracts were washed once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-932c75ba55784221b376e6067a598f27
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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