Bromine → HCID 117678177, compound

HRID 931343Notes

Reaction equation

HRID 931343 reaction equation
[Br:1]Br.[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[CH2:3]([O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([Br:1])=[C:13]([CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 563556HCID 563556, compound

Product 1

HCID 117678177HCID 117678177, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
12 °C

Procedure

A solution of bromine (16 mL, 0.31 mol) in chloroform (100 mL) was added drop-wise to a solution of N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide (see M. P. Leese et al., ACS Med. Chem. Lett. 2012, 3, 5-9) (80 g, 0.27 mol) in chloroform (1 L) at 10-15° C. The reaction mixture was stirred at 12° C. for 10 minutes, then washed sequentially with cooled saturated aqueous sodium bicarbonate solution (2×500 mL) and saturated aqueous sodium chloride solution (400 mL), dried, and concentrated in vacuo. Crystallization of the residue from ethyl acetate afforded the product as a yellow solid. Yield: 90 g, 0.24 mol, 88%. 1H NMR (400 MHz, CDCl3) δ 7.41-7.46 (m, 2H), 7.37 (br dd, J=7.5, 7.0 Hz, 2H), 7.28-7.33 (m, 1H), 7.03 (s, 1H), 6.81 (s, 1H), 5.13 (s, 2H), 3.86 (s, 3H), 3.44-3.52 (m, 2H), 2.89 (t, J=7.0 Hz, 2H), 2.02 (s, 3H).

Workup

  1. washwashed sequentially with cooled saturated aqueous sodium bicarbonate solution (2×500 mL) and saturated aqueous sodium chloride solution (400 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f77d38304edd4f8fb2e51c5a0a9e2af5
Source dataset
uspto-grants-2016_03
Patent number
US09296761B2

Reaction notes

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