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Hydrochloric Acid → (R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetate

HRID 633475
Notes
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Reaction equation

HRID 633475 reaction equation
[OH:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22].Cl>CN(C)C1C=CN=CC=1.ClCCl>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([O:1][C@H:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:3]([O:5][CH3:6])=[O:4])(=[O:32])=[O:31])=[CH:28][CH:29]=1)([O-:23])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

Product 1

HCID 45114280(R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetateYield 98%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

0.72 g (6 mmoles; 0.1 equivalent) of 4-dimethylaminopyridine, 12.0 g (60 mmoles; 1 equivalent) of methyl(R)-2-hydroxy-2(2-chlorophenyl)acetate and 7.8 g (78 mmoles; 1.3 equivalent) of triethylamine and 20 ml of dichloromethane were added to a dry reaction flask. The colorless solution obtained was cooled to 0° C. and then, operating at this temperature, 13.14 g (60 mmoles; 1 equivalent) of 4-nitrobenzenesulfonyl chloride as a solution in 30 ml of dichloromethane was added. The reaction mixture was stirred for 3 hours at 0° C. and 240 ml of 1N hydrochloric acid and 240 ml of dichloromethane was added drop wise, while stirring this mixture. After decanting, the dichloromethane phase is washed with dilute hydrochloric acid and then with water, before being concentrated under reduced pressure. An analytically pure sample is obtained after purifying on a silica column. In this manner, methyl(R)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate is obtained: Yield: 98%. Optical purity: 99%.

Workup

  1. customThe colorless solution obtained
  2. additionwas added
  3. stirringwhile stirring this mixture
  4. customAfter decanting
  5. washthe dichloromethane phase is washed with dilute hydrochloric acid
  6. concentrationwith water, before being concentrated under reduced pressure
  7. customAn analytically pure sample is obtained
  8. customafter purifying on a silica column

Sources & evidence

ORD record
ord-7fff9e5a18f744c89870a6e81b8041c9
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321785B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes