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

HRID 84555Notes

Reaction equation

HRID 84555 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-7a2c80a430114a628573cbc04b17adde
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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