Bromine → HCID 22280043, compound

HRID 1591573Notes

Reaction equation

HRID 1591573 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 MR (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 YYB) The title compound was prepared in the manner analogous to example 1C utilizing compound YYA. 400 MHz 1H NMR (DMSO-d6) δ 7.4 (d, 1H, J=8.8 Hz), 6.80 (d, 1H, 8.8 Hz), 4.84 (s, 2H), 3.64 (s, 3H), 2.78 (m, 2H), 2.59 (m, 2H), 1.70 (m, 4H). MS m/z 278 (m+1). Preparation of (4-Mercapto-5,6,7,8tetrahydro-naphthalen-1-yloxy)-acetic acid methyl ester (compound YY) The title compound was prepared in the manner analogous to example 1D utilizing compound YYB. 400 MHz 1H NMR (DMSO-d6) δ 7.08 (d, 1H, J=8.8 Hz), 6.55 (d, 1H, 8.8 Hz), 4.71 (s, 1H), 4.70 (s, 2H), 3.63 (s, 3H), 2.45 (m, 2H), 2.44 (m, 2H), 1.65 (m, 4H). MS m/z 253 (M+1).

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-ae573b8cc41445b9bf11f9fadeb53cf1
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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