Methanol → HCID 367748, compound

HRID 20610Notes

Reaction equation

HRID 20610 reaction equation
C(O[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br.C[OH:31].O>C(Cl)Cl>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17](=[O:18])[CH:16]=[CH:15][C:11]1[CH:12]=[CH:13][CH:14]=[CH:9][C:10]=1[OH:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 687184593-[3-(Benzyloxy)phenyl]-1-(2-chlorophenyl)prop-2-en-1-one

Product 1

HCID 367748HCID 367748, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 740 mg (2.12 mmol) of 1-4 in 15 mL of CH2Cl2 at −78° C. was added dropwise 2.75 mL (2.75 mmol) of a 1M solution of BBr3 in CH2Cl2. After stirring for 30 min at that temperature, 1 mL of MeOH was added, and the mixture was dumped into water, extracted twice with 50 mL of CH2Cl2, washed again with water, and dried over Na2SO4. After concentration, the residue was purified by column chromatography on silica gel with a gradient of 2 to 70% EtOAc in hexanes over 30 min to provide 1-5 as a beige solid. Data for 1-5: 1HNMR (500 MHz, CDCl3) δ 7.5-7.3 (m, 5H), 7.25 (m, 1H), 7.2-7.0 (m, 3H), 6.9 (m, 1H), 5.1 (bs, 1H) ppm.

Workup

  1. additionwas added
  2. extractionextracted twice with 50 mL of CH2Cl2
  3. washwashed again with water
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by column chromatography on silica gel with a gradient of 2 to 70% EtOAc in hexanes over 30 min

Sources & evidence

ORD record
ord-9c85ea5dd70d457086fcaadda9533b2b
Source dataset
uspto-grants-2010_06
Patent number
US07745639B2

Reaction notes

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