2-Propanethiol → 5-Nitro-2-(propan-2-ylsulfanyl)benzoic acid

HRID 735523Notes

Reaction equation

HRID 735523 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].F[C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].C(N(CC)CC)C>CN(C=O)C>[CH:2]([S:4][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 8471TriethylamineHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 578427985-Nitro-2-(propan-2-ylsulfanyl)benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropylthiol (3.06 mL, 32.8 mmol) was added to a solution of 2-fluoro-5-nitrobenzoic acid (5.06 g, 27.3 mmol) and triethylamine (8.4 mL, 60.3 mmol) in DMF (86 mL). The reaction mixture was stirred overnight at rt and then most of the DMF was removed in vacuo. The residual solution was poured into ice water (500 mL) and the resulting yellow solid was isolated by filtration to give 16A (6.5 g, 100%).

Workup

  1. custommost of the DMF was removed in vacuo
  2. additionThe residual solution was poured into ice water (500 mL)
  3. customthe resulting yellow solid was isolated by filtration

Sources & evidence

ORD record
ord-93b2da06d5d34279905ecd1544080c39
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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