Hydrochloric Acid → HCID 25178693, compound

HRID 1516871Notes

Reaction equation

HRID 1516871 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C(OP([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Br:26])(=O)OCC)C.CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[Br:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1/[CH:19]=[CH:7]/[C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 124815-Chloro-salicylaldehydeHCID 12703598Diethyl [(2-bromophenyl)methyl]phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 25178693HCID 25178693, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Chlorosalicylaldehyde (188 g, 1.2 mol) was added to a solution of (2-bromo-benzyl)-phosphonic acid diethyl ester (369 g, 1.2 mol) in tetrahydrofuran (1500 ml) under nitrogen. A solution of potassium tert-butoxide (300 g, 2.68 mol) in tetrahydrofuran (3000 ml) was added while keeping the temperature at 33° C. After completion of the reaction water (1800 ml) was added followed by 4N HCl (450 ml). The organic layer was washed with sodium carbonate solution (500 ml) and saturated NaCl solution. The organic layer was evaporated under reduced pressure at 50° C. to give trans-2-bromo-5′-chloro-2′-hydroxystilbene (301.9 g, 92%).

Workup

  1. customat 33° C
  2. additionwas added
  3. washThe organic layer was washed with sodium carbonate solution (500 ml) and saturated NaCl solution
  4. customThe organic layer was evaporated under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1d32674392994d069fbdff3678b17efe
Source dataset
uspto-grants-2012_07
Patent number
US08227623B2

Reaction notes

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