Water → HCID 9910377, compound

HRID 611737Notes

Reaction equation

HRID 611737 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][C:30](=[O:33])[CH2:31]Br.O>CN(C)C=O>[CH3:28][O:29][C:30](=[O:33])[CH2:31][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:3]2[C:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[S:6][C:5]=3[CH:13]=[CH:14][C:2]=2[Br:1])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 9928561HCID 9928561, compound

Product 1

HCID 9910377HCID 9910377, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-bromo-dibenzothiophen-1-yl)-phenol (0.480 g, 1.35 mmol) and potassium carbonate (0.385 g, 2.79 mmol, 2.06 eq) in anhydrous N,N-dimethylformamide (3 mL) was added methylbromoacetate (0.255 mL, 2.07 mmol, 2 eq) dropwise at room temperature under a dry nitrogen atmosphere. After stirring 24 hours the reaction mixture was poured into water (100 mL) and the organics were extracted into ether (100 mL) The ether was washed with water (100 mL) and brine (100 mL). Silica gel was added and the solvents removed. The adsorbate was flash chromatographed (55/45 petroleum ether/methylene chloride) and dried in vacuo at 58° C. to provide the title compound as a white solid (0.509 g, 88%); mp 122-122.5° C. NMR (DMSO-d6), δ 8.02 (d, J=8 Hz, 1H), 8.00 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.41 (t, J=8 Hz, 1H), 7.26-7.20 (m, 2H), 7.19 -7.16 (m, 2H), 7.13-7.09 (ddd, J=8,7,1, 1H), 6.53 (d, J=8 Hz 1H), 4.94 (s, 2H), 3.75 (s, 3H), MS [PBEI] M*+ m/z=426(100%), 428(98%), 1 bromine isotope pattern detected, Anal. Calc. for C21H15O3SBr: C, 59.03, H, 3.54, N, 0.00. Found: C, 58.91, H, 3,27, N, -0.02.

Workup

  1. extractionthe organics were extracted into ether (100 mL) The ether
  2. washwas washed with water (100 mL) and brine (100 mL)
  3. additionSilica gel was added
  4. customthe solvents removed
  5. customchromatographed (55/45 petroleum ether/methylene chloride)
  6. customdried in vacuo at 58° C.

Sources & evidence

ORD record
ord-13eec46fdff2485887f3d275ea9b43b5
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

Loading…