Anisole → HCID 12804500, compound

HRID 1660099Notes

Reaction equation

[F:1][C:2](S(O)(=O)=O)([F:4])[F:3].[K+].[Br-].CCC[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:24][CH2:25]N2CCCCC2)=O)=[CH:18][CH:17]=1.Cl.[C:33]1([O:39][CH3:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:40][O:39][C:33]1[CH:38]=[CH:37][C:36]([C:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=2)([C:24]2[CH:25]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[C:2]([F:4])([F:3])[F:1])=[CH:35][CH:34]=1

Participants

Reactant 4

HCID 7519Anisole

HCID 62406Trifluoromethanesulfonic acid

HCID 68304Dyclonine hydrochloride

HCID 253877Potassium Bromide

Product 1

HCID 12804500HCID 12804500, compound

Procedure

A solution of 9.0 g (0.044 mol) of 4-methoxy-α,α,α-trifluoroacetophenone, 90 ml of anisole and 5 ml of trifluoromethyl sulfonic acid was stirred for 48 hours. At the end of this period, the product was worked up as in Example 6 to give 14.2 g (80%) of white crystalline 9; m.p. 196°-197° C., IR (KBr) 3010 (C--H, ar), 2840 (OCH3), 1610 and 1510 (Ar), 1150 (C--F) 825 cm-1 (parasubstituted phenyl); NMR δ 3.80 (s, 3H), 6.75 (d, J=8 Hz, 2H); 7.05 (d, J=8 Hz 2H); mass spectrum m/e, 402 (parent ion), 333 (P-69), 163 (P-239), 135 (P-267). Analytical: calculated for C23H2O3F3 ; C, 68.65; H, 5.22; F, 14.2%. Found: C, 68.48; H, 530; F, 14.2%.

Workup

customto give 14.2 g (80%) of white crystalline 9

Sources & evidence

ORD record: ord-3e685faf6e884b86923d2ad54b3f6360
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04307024

Reaction notes

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