3,4-dihydro-2H-pyran → 4-Bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid 4-bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

HRID 2098894Notes

Reaction equation

HRID 2098894 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1.[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 674295254-Bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid 4-bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 4-bromo-3-hydroxybenzoic acid (G.1) (available from Combi-Blocks Inc.) (2.50 g, 115 mmol) in DCM (100 mL) at 23° C., was added 3,4-dihydro-2H-pyran (2.10 mL, 23.0 mmol) followed by PPTS (0.289 g, 1.15 mmol). The reaction gave a mixture of bis THP protected compound and G.2.

Workup

  1. customThe reaction gave
  2. additiona mixture of bis THP protected compound and G.2

Sources & evidence

ORD record
ord-4da92d7af57d429aa4a30f0770752302
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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