HCID 59829157, compound → HCID 59829145, compound

HRID 2061409Notes

Reaction equation

HRID 2061409 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:20])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH:5]=[O:6].[CH:21]([Mg]Br)=[CH2:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH:21]=[CH2:22])[CH:7]=[C:8]([Br:20])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 59829157HCID 59829157, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 59829145HCID 59829145, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,5-dibromo-4-(4-methoxybenzyloxy)benzaldehyde (C) (3.04 g, 7.60 mmol) in anhydrous THF (40 mL) under nitrogen, cooled to −76° C., was added dropwise over 15 min vinylmagnesium bromide (1.0 M solution in THF, 11.4 mL, 11.4 mmol), keeping the internal temperature below −70° C. The mixture was stirred at <−70° C. for 65 min, and then quenched with saturated aqueous ammonium chloride solution (6 mL). The stirred mixture was allowed to warm to room temperature, and then partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with saturated aqueous sodium chloride (80 mL), dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (silica gel, 15% EtOAc/pet. ether) to give 2.45 g (75%) of the title compound as a colourless oil. 1H NMR δ (ppm) (CDCl3): 1.96 (1 H, d, J=3.75 Hz), 3.83 (3 H, s), 4.96 (2 H, s), 5.14 (1 H, t, J=4.58 Hz), 5.27 (1 H, d, J=10.29 Hz), 5.35-5.42 (1 H, m), 5.98 (1 H, ddd, J=17.08, 10.28, 6.28 Hz), 6.90-6.96 (2 H, m), 7.50-7.57 (4 H, m).

Workup

  1. customthe internal temperature below −70° C
  2. customquenched with saturated aqueous ammonium chloride solution (6 mL)
  3. custompartitioned between ethyl acetate (200 mL) and water (200 mL)
  4. washThe organic layer was washed with saturated aqueous sodium chloride (80 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 15% EtOAc/pet. ether)

Sources & evidence

ORD record
ord-673a464f5e33438a920d73dbd16504eb
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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