Acetic Acid → HCID 71230691, compound

HRID 2199573Notes

Reaction equation

HRID 2199573 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:12][CH:11]=1.C(O)(=O)C.C1C(=O)N([Br:38])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:38][C:18]1[S:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:6]3[S:7][CH:8]=[CH:9][C:5]=3[CH2:4][C:3]([O:2][CH3:1])=[O:26])=[CH:11][CH:12]=2)=[C:20]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 71230677HCID 71230677, compound

Product 1

HCID 71230691HCID 71230691, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate R (1.13 g, 2.92 mmol) was dissolved in CHCl3 (5 ml), acetic acid (5 ml) was added and the solution was cooled to 0° C. NBS (0.53 g, 2.92 mmol) was added and the mixture was left to slowly reach ambient temperature. After 14 hrs, the reaction mixture was diluted with CH2Cl2 (20 ml), washed with water/brine (30:1-60 ml), dried with MgSO4 (s), filtered and evaporated to dryness to obtain the crude product. The residue was purified by flash chromatography using toluene/EtOAc 100:1→40:1) as eluent. Yield: 0.54 g (40%); off-white solid. 1H NMR (400 MHz, CDCl3): δ 3.63 (s, 2H), 3.69 (s, 2H), 3.73 (s, 3H), 3.74 (s, 3H), 7.06 (s, 1H), 7.09 (d, J 5.3 Hz, 1H), 7.30 (d, J 5.3 Hz, 1H), 7.45-7.48 (m, 2H), 7.51-7.54 (m, 2H).

Workup

  1. waitthe mixture was left to slowly reach ambient temperature
  2. washwashed with water/brine (30:1-60 ml)
  3. dry with materialdried with MgSO4 (s)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f04e5cdaec364dc58cfada3efef14659
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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