Bromine → HCID 57437427, compound

HRID 1665944Notes

Reaction equation

HRID 1665944 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2].[Br:17]Br>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([Br:17])=[C:9]2[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 57508883Ethyl 4,5,6,7-tetrahydro-5,5-dimethylbenzo[c]thiophene-1-carboxylate

Product 1

HCID 57437427HCID 57437427, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester (715 mg, 3.0 mmol) in acetic acid (5 mL), bromine (480 mg, 3.0 mmol) is slowly added at rt. Upon completion of the addition, the mixture is heated to 50° C. and stirred for 4 h. The reaction is quenched by adding 1 N aq. NaOH and the mixture is extracted with DCM (3×50 mL). The organic extracts are dried (Na2SO4), filtered and evaporated to provide crude 3-bromo-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid ethyl ester (774 mg) as a brown oil; 1H NMR (CDCl3): δ 4.27 (q, J=7.6 Hz, 2H), 2.97 (t, J=7.0 Hz, 2H), 2.26 8s, 2H), 1.51 (t, J=7.0 Hz, 2H), 1.33 8t, J=7.6 Hz, 3H), 0.95 (s, 6H).

Workup

  1. additionUpon completion of the addition
  2. customThe reaction is quenched
  3. additionby adding 1 N aq. NaOH
  4. extractionthe mixture is extracted with DCM (3×50 mL)
  5. dry with materialThe organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-800b181f44214628a9d6d843abee0d07
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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