Bromochloromethane → HCID 118037775, compound

HRID 587912Notes

Reaction equation

HRID 587912 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]([O:10][CH2:11][O:12][CH2:13][CH3:14])=[CH:4][C:3]=1[CH:15]([OH:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Br[CH2:23]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:13]([O:12][CH2:11][O:10][C:5]1[CH:4]=[C:3]([CH:15]([OH:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]2[O:1][CH2:23][O:8][C:7]=2[C:6]=1[CH3:9])[CH3:14]

Participants

5

Reactant 3

HCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 131734425HCID 131734425, compound

Product 1

HCID 118037775HCID 118037775, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By following Example 9 procedure, 0.19 g of ethyl 2-(2,3-dihydroxy-5-(ethoxymethoxy)-4-methylphenyl)-2-hydroxyacetate is reacted with 1.0 g of bromochloromethane and 0.65 g of cesium carbonate in DMF medium to get 0.086 g of title compound as syrup. IR (neat): 3481, 2978, 2928, 1739, 1492, 1435, 1397, 1365, 1255, 1209, 1117, 1058, 984, 936, 847, and 718 cm−1. 1H-NMR (CDCl3, 400 MHz): δ 6.51 (s, 1H, Ar. H), 5.96 (d, J=1.2 Hz, 1H, OCH2O), 5.92 (d, J=1.2 Hz, 1H, OCH2O), 5.17 (br. s., exch. with D2O, 1H, OH), 5.15 (d, J=1.6 Hz, 2H, ArOCH2O), 4.19-4.30 (m, 2H, OCH2OCH2CH3), 3.72 (q, J=6.8 Hz, 2H, COOCH2CH3), 2.10 (s, 3H, ArCH3), 1.25 (t, J=7.2 Hz, 3H, OCH2CH3), 1.23 (t, J=7.2 Hz, 3H, OCH2CH3). 13C NMR (CDCl3, 100 MHz): δ 173.04 (CO), 151.26 (C-6), 146.70 (C-1a), 139.58 (C-3a), 116.38 (C-4), 110.94 (C-7), 105.55 (C-5), 101.30 (C-2), 94.43 (OCH2O), 68.83 (CHOH), 64.29 (OCH2CH3), 62.17 (OCH2CH3), 15.09 (OCH2CH3), 14.04 (OCH2CH3), 8.96 (ArCH3)

Sources & evidence

ORD record
ord-81bc20c37a194f709c3a66a058689426
Source dataset
uspto-grants-2016_01
Patent number
US09227948B2

Reaction notes

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