Methanol → Methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate

HRID 2069646Notes

Reaction equation

HRID 2069646 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([C:17]([OH:19])=[O:18])[C:9]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10]=2[CH:16]=1.[CH3:20]O>>[Br:5][C:6]1[CH:7]=[C:8]([C:17]([O:19][CH3:20])=[O:18])[C:9]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10]=2[CH:16]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 148384015-Bromo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acid

Product 1

HCID 58566735Methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate

Procedure

Thionyl chloride (0.6 mL, 8.12 mmol) was added slowly to a solution of 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (667) (1.1 g, 4.06 mmol) in methanol (41 mL). After refluxing for 3 hours the solvent was removed in vacuo to obtain methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (668).

Workup

  1. temperatureAfter refluxing for 3 hours the solvent
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-c9545567856c49839f987327113c3508
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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