Water → HCID 10514484, compound

HRID 1737300Notes

Reaction equation

HRID 1737300 reaction equation
[OH:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[Br:13]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:13][C:9]1[CH:8]=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH2:3][C:2]([OH:1])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 106309013-(2-Hydroxy-2-methylpropyl)phenol

Product 1

HCID 10514484HCID 10514484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Alcohol 29 (12.3 g, 74.2 mmol) is dissolved in dry DMF and cooled to 0° C. under N2. Solid N-bromosuccinimide (NBS, 14.77 g, 83.0 mmol) is added in small portions (the yellow color is allowed to dissipate between additions) over 1.5 h. After the addition is complete, stirring at 0° C. is continued for 30 min. The mixture is then poured into water and extracted with EtOAc (3×). The organic phase is washed with water (1×) and brine (1×), dried (MgSO4), filtered, and evaporated. The residue is dissolved in EtOAc/CH2Cl2 and diluted with hexane to afford 30 as white crystals, mp 139-141° C. (12.7 g, 70%). Concentration of the mother liquor gives two more crops (1.2 and 1.0 g) of crystals, bringing the total to 14.9 g (82%). 1H NMR (acetone-d6, 2.05 ppm) 8.43 (S,1), 7.34 (d, 1, J=8.7), 7.01 (d, 1, J=2.7), 6.64 (dd, 1, J=8.7, 2.8), 2.89 (s,2), 1.21 (s,6); 13C NMR (acetone-d6, 20.83 ppm) 147.90, 130.98, 124.56, 111.34, 107.05, 106.19, 62.35, 39.59, 20.76; MS (EI, eE=70 eV) m/z 246/244 (M+), 231/229, 201, 188/186, 163, 150, 131, 108, 107, 91, 77, 63, 59 (base peak), 51, 43; Anal. Calcd for C10H13BrO2 (MW=245.1) : C,49.00 H,5.35. Found: C,49.03 H,5.20.

Workup

  1. customover 1.5 h
  2. additionAfter the addition
  3. extractionextracted with EtOAc (3×)
  4. washThe organic phase is washed with water (1×) and brine (1×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue is dissolved in EtOAc/CH2Cl2
  9. additiondiluted with hexane

Sources & evidence

ORD record
ord-c740995ced2f4ee18cbbce46b8ac2d70
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

Loading…