Acetic Anhydride → HCID 13920896, compound

HRID 246998Notes

Reaction equation

HRID 246998 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:9](=[O:11])([S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH3:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 805982-Bromobenzenethiol

Product 1

HCID 13920896HCID 13920896, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-bromothiophenol (100 g, 0.529 mol), acetic anhydride (62.4 mL, 0.661 mol), and 4-dimethylaminopyridine (3.2 g, 0.026 mol) in dichloromethane (1000 mL) was cooled in an ice-bath. Triethylamine (92.2 mL, 0.662 mol) was slowly added, and then the ice bath was removed. The mixture was stirred at room temperature for 1 hour. Water (10 mL) was added, and after a couple of minutes the mixture was washed with aqueous 1N hydrochloric acid (3×300 mL), 10% sodium hydroxide solution (3×300 mL), and 1N hydrochloric acid (300 mL), and then dried (Na2SO4), and filtered. Evaporation of the solvent left S-2-bromophenyl ethanethioate as a pale yellow oil (104 g).

Workup

  1. customthe ice bath was removed
  2. additionWater (10 mL) was added
  3. washafter a couple of minutes the mixture was washed with aqueous 1N hydrochloric acid (3×300 mL), 10% sodium hydroxide solution (3×300 mL), and 1N hydrochloric acid (300 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customEvaporation of the solvent
  7. waitleft S-2-bromophenyl ethanethioate as a pale yellow oil (104 g)

Sources & evidence

ORD record
ord-6db3b4b77b5e4846a3952a1b96d79ddb
Source dataset
uspto-grants-1987_11
Patent number
US04705555

Reaction notes

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