Ethanol → 9-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid

HRID 627974Notes

Reaction equation

HRID 627974 reaction equation
C([O:3][C:4]([C:6]1[S:15][C:14]2[C:13]3[CH:16]=[C:17]([Br:20])[CH:18]=[CH:19][C:12]=3[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+].CCO>C1COCC1.O>[Br:20][C:17]1[CH:18]=[CH:19][C:12]2[O:11][CH2:10][CH2:9][C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[S:15][C:14]=3[C:13]=2[CH:16]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 668685979-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid ethyl ester

Product 1

HCID 668685729-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid ethyl ester (4.24 g; 12 mmol) in THF (40 ml) at room temperature was added a solution of NaOH (0.96 g; 24 mmol) in water (20 ml) followed by EtOH (20 ml). The reaction mixture was stirred at room temperature for 4 h (now a clear solution) upon which time it was quenched with 2M HCl (20 ml) and diluted with water (50 ml). The resulting solid was collected by filtration, washed with water and dried to give 9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid as a white solid (3.64 g; 93%). δH (400 MHz, d6-DMSO) 3.22 (t, J=5.2, 2H), 4.31 (t, J=5.2, 2H), 7.02 (d, J=8.4, 1H), 7.43 (dd, J=8.4 and 2.4, 1H), 7.62 (s, 1H), 7.78 (d, J=2.4, 1H).

Workup

  1. customwas quenched with 2M HCl (20 ml)
  2. additiondiluted with water (50 ml)
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e85e8d8f944f447b9657432b166e2a01
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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