Sodium Hydroxide → 2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-carboxylic acid
Reaction equation
Br[O-].[Na+].BrBr.[OH-].[Na+].[C:8]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][CH2:31][CH2:32][Br:33])=[CH:22][CH:21]=1)(=[O:10])C.S(=O)(O)[O-:35].[Na+]>O.O1CCOCC1>[C:8]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][CH2:31][CH2:32][Br:33])=[CH:22][CH:21]=1)([OH:10])=[O:35]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of sodium hypobromite, prepared by adding 2.45 g. (0.45 mol.) of bromine to a cooled (0°) solution of 4.5 g. (0.1125 mol.) of sodium hydoxide in 40 ml. of water, was added to a solution of 6.1 g. (0.015 mol.) of 3-acetyl-2-[4-(2-bromoethoxy)naphthyl]benzofuran in 60 ml. of dioxane and the mixture was shaken for 12 hours. Sodium bisulfite was added to the reaction mixture, water was added and the mixture was extracted twice with ether. The aqueous phase was acidified with hydrochloric acid, the resulting precipitate was digested on a steam bath for 1 hour, cooled to 0° and collected by filtration to give 3-carboxy-2-[4-(2-bromo-ethoxy)naphthyl]benzofuran, m.p. 260°-265° (dec.).
Workup
- additionby adding 2.45 g
- additionwas added
- extractionthe mixture was extracted twice with ether
- temperaturecooled to 0°
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-517b80626db2429f8b30a3a513baeedd
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03985896
Reaction notes
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