2,6-Lutidine → 6-Hydroxy-benzofuran-4-carboxylic acid methyl ester

HRID 1643548Notes

Reaction equation

HRID 1643548 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]2[O:13][CH:12](C)[CH2:11][C:10]=12)=[O:4].N1C(C)=CC=CC=1C.B(Br)(Br)Br.COC(C1C=C(OC)C=C2OC=CC=12)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=[O:4]

Participants

5

Reactant 4

HCID 79372,6-LutidineHCID 25134Boron tribromideHCID 595598666-Hydroxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl esterHCID 595600184-Benzofurancarboxylic acid, 6-methoxy-, methyl ester

Product 1

HCID 595601586-Hydroxy-benzofuran-4-carboxylic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1e, from 2,6-lutidine (1.42 mL, 12.2 mmol), BBr3 (12.2 mL, 12.2 mmol, 1.0 M in CH2Cl2) and 6-methoxy-benzofuran-4-carboxylic acid methyl ester (6c) (840 mg, 4.07 mmol). Purification by flash column chromatography (10-15% EtOAc in hexanes) gave a pale yellow solid (350 mg, 45% yield). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=2.27 Hz, 1 H) 7.61 (d, J=2.02 Hz, 1 H) 7.24 (dd, J=3.28, 2.27 Hz, 2 H) 5.66 (s, 1 H) 4.00 (s, 3 H).

Workup

  1. customPurification by flash column chromatography (10-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d4d879f5af704811a0792c01e8708eae
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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